# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_cf3sz
_database_code_depnum_ccdc_archive 'CCDC 2179670'
loop_
_audit_author_name
_audit_author_address
ZZP
;Fuzhou University
China
;
_audit_update_record             
;
2022-06-17 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_audit_creation_date             2021-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        P-1
_chemical_formula_moiety         'C8 H6 F3 N O4 S'
_chemical_formula_sum            'C8 H6 F3 N O4 S'
_chemical_formula_weight         269.20
_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'
F F 0.0171 0.0103 '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      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                   7.7049(7)
_cell_length_b                   8.0698(6)
_cell_length_c                   9.0862(8)
_cell_angle_alpha                74.601(3)
_cell_angle_beta                 77.073(3)
_cell_angle_gamma                82.099(3)
_cell_volume                     529.03(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9969
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.049
_cell_measurement_theta_min      2.371
_shelx_estimated_absorpt_T_max   0.996
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.352
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6638
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            15440
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         2.371
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1807
_reflns_number_total             1877
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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         0.316
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.044(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         1877
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.043
_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)+(0.0312P)²+0.2814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0652
_refine_ls_wR_factor_ref         0.0658
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C5(H5A,H5B,H5C), C7(H7A,H7B,H7C)
;
_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
S1 S 0.16615(5) 0.72814(4) 0.51791(4) 0.02247(14) Uani 1 1 d . . . . .
F3 F 0.24776(14) 0.93432(13) 0.09688(11) 0.0422(3) Uani 1 1 d . . . . .
F1 F 0.05388(15) 1.01752(12) 0.27578(11) 0.0423(3) Uani 1 1 d . . . . .
O2 O 0.47523(15) 0.29070(13) 0.28044(12) 0.0308(3) Uani 1 1 d . . . . .
O3 O 0.39611(14) 0.28953(14) 0.71145(12) 0.0305(3) Uani 1 1 d . . . . .
O4 O 0.20767(15) 0.48817(14) 0.81440(12) 0.0296(3) Uani 1 1 d . . . . .
F2 F -0.01747(16) 0.85485(13) 0.15147(14) 0.0527(3) Uani 1 1 d . . . . .
O1 O 0.26449(15) 0.15445(13) 0.47092(14) 0.0335(3) Uani 1 1 d . . . . .
N1 N 0.22275(15) 0.58320(15) 0.28916(13) 0.0214(3) Uani 1 1 d . . . . .
C6 C 0.29287(19) 0.41567(18) 0.69910(16) 0.0225(3) Uani 1 1 d . . . . .
C2 C 0.26753(18) 0.46086(18) 0.41458(16) 0.0200(3) Uani 1 1 d . . . . .
C4 C 0.33307(19) 0.28257(18) 0.39501(16) 0.0221(3) Uani 1 1 d . . . . .
C1 C 0.16789(18) 0.72766(18) 0.32963(16) 0.0211(3) Uani 1 1 d . . . . .
C3 C 0.24533(18) 0.51514(17) 0.54872(16) 0.0204(3) Uani 1 1 d . . . . .
C8 C 0.1121(2) 0.88420(19) 0.21310(17) 0.0255(3) Uani 1 1 d . . . . .
C5 C 0.5540(3) 0.1272(2) 0.2465(2) 0.0386(4) Uani 1 1 d . . . . .
H5A H 0.661308 0.145829 0.168778 0.058 Uiso 1 1 calc GR . . . .
H5B H 0.470702 0.078705 0.208787 0.058 Uiso 1 1 calc GR . . . .
H5C H 0.582062 0.049043 0.339710 0.058 Uiso 1 1 calc GR . . . .
C7 C 0.2576(3) 0.4096(2) 0.96421(19) 0.0439(5) Uani 1 1 d . . . . .
H7A H 0.384555 0.408100 0.953338 0.066 Uiso 1 1 calc GR . . . .
H7B H 0.222826 0.293609 1.000374 0.066 Uiso 1 1 calc GR . . . .
H7C H 0.198228 0.475112 1.037908 0.066 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
S1 C1 1.7088(14) . ?
S1 C3 1.7139(14) . ?
F3 C8 1.3291(18) . ?
F1 C8 1.3272(17) . ?
O2 C4 1.3271(18) . ?
O2 C5 1.4550(18) . ?
O3 C6 1.1992(18) . ?
O4 C6 1.3353(18) . ?
O4 C7 1.4531(19) . ?
F2 C8 1.3238(18) . ?
O1 C4 1.1967(18) . ?
N1 C2 1.3701(18) . ?
N1 C1 1.3021(18) . ?
C6 C3 1.4853(19) . ?
C2 C4 1.5009(19) . ?
C2 C3 1.370(2) . ?
C1 C8 1.498(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
C1 S1 C3 88.43(7) . . ?
C4 O2 C5 116.06(12) . . ?
C6 O4 C7 114.87(13) . . ?
C1 N1 C2 109.24(12) . . ?
O3 C6 O4 125.95(13) . . ?
O3 C6 C3 123.45(13) . . ?
O4 C6 C3 110.59(12) . . ?
N1 C2 C4 118.51(12) . . ?
C3 C2 N1 115.40(12) . . ?
C3 C2 C4 126.09(13) . . ?
O2 C4 C2 109.51(12) . . ?
O1 C4 O2 126.07(13) . . ?
O1 C4 C2 124.41(13) . . ?
N1 C1 S1 116.82(11) . . ?
N1 C1 C8 120.25(12) . . ?
C8 C1 S1 122.92(10) . . ?
C6 C3 S1 122.24(10) . . ?
C2 C3 S1 110.10(10) . . ?
C2 C3 C6 127.51(13) . . ?
F3 C8 C1 111.31(12) . . ?
F1 C8 F3 106.71(12) . . ?
F1 C8 C1 112.08(12) . . ?
F2 C8 F3 107.40(13) . . ?
F2 C8 F1 107.40(13) . . ?
F2 C8 C1 111.67(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_yyf20220630-1_auto
_database_code_depnum_ccdc_archive 'CCDC 2183006'
loop_
_audit_author_name
_audit_author_address
'Yunfei Yao'
;Fuzhou University
China
;
_audit_update_record             
;
2022-06-30 deposited with the CCDC.	2022-10-14 downloaded from the CCDC.
;
_audit_creation_date             2022-06-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H12 F3 N O3 S'
_chemical_formula_sum            'C18 H12 F3 N O3 S'
_chemical_formula_weight         379.35
_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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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           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                   4.8566(2)
_cell_length_b                   35.3036(13)
_cell_length_c                   10.3267(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.951(4)
_cell_angle_gamma                90
_cell_volume                     1757.56(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      65.9680
_cell_measurement_theta_min      2.5000
_shelx_estimated_absorpt_T_max   0.818
_shelx_estimated_absorpt_T_min   0.818
_exptl_absorpt_coefficient_mu    2.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
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    1.434
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.1
_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  0.0283
_diffrn_reflns_av_unetI/netI     0.0364
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8045
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.266
_diffrn_reflns_theta_min         2.503
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -44.00 -10.00   0.50    2.00    --   42.50 -32.00  90.00   68
  2  ω     14.00  70.00   0.50    2.00    --   42.50 -54.00 -90.00  112
  3  ω     89.00 120.00   0.50    2.00    --   42.50  82.00-150.00   62
  4  ω     28.00  74.00   0.50    2.00    --   42.50 -32.00  90.00   92
  5  ω    -46.00  27.00   0.50    2.00    --   42.50 -77.00  60.00  146
  6  ω     32.00  66.00   0.50    2.00    --   42.50 -77.00  60.00   68
  7  ω     16.00  84.00   0.50    2.00    --   42.50  82.00-150.00  136
  8  ω     19.00  66.00   0.50    2.00    --   42.50 -77.00 -90.00   94
  9  ω     70.00 121.00   0.50    2.00    --   42.50  65.00  30.00  102
 10  ω    -33.00  -8.00   0.50    2.00    --   42.50 -54.00 -90.00   50
 11  ω      5.00  87.00   0.50    2.00    --   93.70 -59.00  90.00  164
 12  ω     38.00  64.00   0.50    2.00    --   93.70 -50.00-120.00   52
 13  ω     52.00 121.00   0.50    2.00    --   93.70 -59.00   0.00  138
 14  ω     45.00  93.00   0.50    2.00    --   93.70 -82.00-150.00   96
 15  ω      6.00  32.00   0.50    2.00    --   93.70 -59.00   0.00   52
 16  ω     62.00 113.00   0.50    2.00    --   93.70 -82.00 -90.00  102
 17  ω      4.00  44.00   0.50    2.00    --   93.70 -82.00 -90.00   80
 18  ω     87.00 183.00   0.50    2.00    --   93.70  33.00-150.00  192
 19  ω     70.00 116.00   0.50    2.00    --   93.70 -50.00-120.00   92
 20  ω     90.00 116.00   0.50    2.00    --   93.70 -82.00-180.00   52
 21  ω     10.00  88.00   0.50    2.00    --   93.70 -42.00   0.00  156
 22  ω     23.00 119.00   0.50    2.00    --   93.70 -59.00 150.00  192
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Pro II AFC12 (RINC): Kappa dual offset/far'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1242100000
_diffrn_orient_matrix_UB_12      0.0060634000
_diffrn_orient_matrix_UB_13      0.1429869000
_diffrn_orient_matrix_UB_21      -0.0561275000
_diffrn_orient_matrix_UB_22      -0.0418648000
_diffrn_orient_matrix_UB_23      0.0297753000
_diffrn_orient_matrix_UB_31      0.2889771000
_diffrn_orient_matrix_UB_32      -0.0107299000
_diffrn_orient_matrix_UB_33      -0.0354856000
_diffrn_oxdiff_digest_frames     
;
014b9febac2010ef93a33cbced70267b3a00026ff68
;
_diffrn_oxdiff_digest_hkl        
;
010720270b8c0930370c0c08e546ac027f141e
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\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         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1975
_reflns_number_total             3167
_reflns_odcompleteness_completeness 99.56
_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 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0630
_refine_ls_restrained_S_all      1.098
_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)+(0.1255P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2008
_refine_ls_wR_factor_ref         0.2214
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00P(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00E(H00E), C00J(H00J), C00K(H00K), C00M(H00M), C00N(H00N),
 C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00Q(H00D,H00F,H00G)
;
_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
S001 S 0.2715(2) 0.37264(3) 0.82394(9) 0.0882(4) Uani 1 1 d . . . . .
O002 O 0.8176(5) 0.39903(6) 0.5087(2) 0.0812(7) Uani 1 1 d . . . . .
O003 O 0.5772(6) 0.45312(6) 0.4941(3) 0.0986(9) Uani 1 1 d . . . . .
N004 N 0.3478(6) 0.43603(7) 0.7131(3) 0.0711(7) Uani 1 1 d . . . . .
O005 O 0.7149(7) 0.31699(7) 0.7302(3) 0.1098(10) Uani 1 1 d . . . . .
F006 F -0.0887(7) 0.46809(9) 0.8346(3) 0.1532(12) Uani 1 1 d . . . . .
F007 F 0.2502(7) 0.46496(10) 0.9719(3) 0.1741(15) Uani 1 1 d . . . . .
C008 C 0.4970(7) 0.32301(7) 0.5139(3) 0.0650(8) Uani 1 1 d . . . . .
C009 C 0.4766(6) 0.40890(8) 0.6483(3) 0.0648(8) Uani 1 1 d . . . . .
C00A C 0.6417(7) 0.41914(8) 0.5418(3) 0.0670(8) Uani 1 1 d . . . . .
C00B C 0.2136(7) 0.32682(9) 0.3047(3) 0.0679(8) Uani 1 1 d . . . . .
C00C C 0.2904(6) 0.33979(8) 0.4326(3) 0.0658(8) Uani 1 1 d . . . . .
H00C H 0.197548 0.360429 0.462715 0.079 Uiso 1 1 calc R . . . .
C00D C 0.4545(7) 0.37259(8) 0.6926(3) 0.0677(8) Uani 1 1 d . . . . .
C00E C 0.6392(7) 0.29146(8) 0.4683(4) 0.0796(10) Uani 1 1 d . . . . .
H00E H 0.784037 0.280223 0.521919 0.096 Uiso 1 1 calc R . . . .
C00F C 0.5699(7) 0.33574(9) 0.6497(3) 0.0753(9) Uani 1 1 d . . . . .
C00G C 0.2341(7) 0.42071(10) 0.8068(4) 0.0785(9) Uani 1 1 d . . . . .
C00H C 0.3529(8) 0.29473(9) 0.2610(3) 0.0751(9) Uani 1 1 d . . . . .
F00I F -0.0711(10) 0.42399(10) 0.9628(4) 0.1931(18) Uani 1 1 d . . . . .
C00J C 0.5643(9) 0.27788(10) 0.3478(4) 0.0912(12) Uani 1 1 d . . . . .
H00J H 0.654996 0.256639 0.320585 0.109 Uiso 1 1 calc R . . . .
C00K C 0.0036(8) 0.34402(11) 0.2190(4) 0.0899(11) Uani 1 1 d . . . . .
H00K H -0.088135 0.365052 0.247086 0.108 Uiso 1 1 calc R . . . .
C00L C 0.0877(10) 0.44333(15) 0.8984(4) 0.1067(14) Uani 1 1 d . . . . .
C00M C 0.2713(11) 0.28144(12) 0.1322(5) 0.1037(13) Uani 1 1 d . . . . .
H00M H 0.359844 0.260488 0.101605 0.124 Uiso 1 1 calc R . . . .
C00N C -0.0691(10) 0.33067(14) 0.0958(4) 0.1070(14) Uani 1 1 d . . . . .
H00N H -0.207506 0.342524 0.040001 0.128 Uiso 1 1 calc R . . . .
C00O C 0.0689(12) 0.29861(13) 0.0544(4) 0.1113(15) Uani 1 1 d . . . . .
H00O H 0.018119 0.289148 -0.029107 0.134 Uiso 1 1 calc R . . . .
C00P C 0.7335(12) 0.46618(12) 0.3898(5) 0.1159(16) Uani 1 1 d . . . . .
H00A H 0.742385 0.493626 0.389821 0.139 Uiso 1 1 calc R . . . .
H00B H 0.921455 0.456401 0.403761 0.139 Uiso 1 1 calc R . . . .
C00Q C 0.5948(15) 0.45272(17) 0.2652(6) 0.158(2) Uani 1 1 d . . . . .
H00D H 0.696866 0.460826 0.196155 0.236 Uiso 1 1 calc GR . . . .
H00F H 0.410328 0.462923 0.251265 0.236 Uiso 1 1 calc GR . . . .
H00G H 0.585757 0.425561 0.266126 0.236 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 C00D 1.709(4) . ?
S001 C00G 1.714(4) . ?
O002 C00A 1.192(4) . ?
O003 C00A 1.320(4) . ?
O003 C00P 1.465(5) . ?
N004 C009 1.363(4) . ?
N004 C00G 1.289(4) . ?
O005 C00F 1.218(4) . ?
F006 C00L 1.340(5) . ?
F007 C00L 1.280(5) . ?
C008 C00C 1.363(4) . ?
C008 C00E 1.421(4) . ?
C008 C00F 1.474(5) . ?
C009 C00A 1.482(4) . ?
C009 C00D 1.370(4) . ?
C00B C00C 1.405(4) . ?
C00B C00H 1.421(5) . ?
C00B C00K 1.405(5) . ?
C00C H00C 0.9300 . ?
C00D C00F 1.505(4) . ?
C00E H00E 0.9300 . ?
C00E C00J 1.342(5) . ?
C00G C00L 1.483(5) . ?
C00H C00J 1.410(5) . ?
C00H C00M 1.421(5) . ?
F00I C00L 1.276(5) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00N 1.363(5) . ?
C00M H00M 0.9300 . ?
C00M C00O 1.337(6) . ?
C00N H00N 0.9300 . ?
C00N C00O 1.408(7) . ?
C00O H00O 0.9300 . ?
C00P H00A 0.9700 . ?
C00P H00B 0.9700 . ?
C00P C00Q 1.458(8) . ?
C00Q H00D 0.9600 . ?
C00Q H00F 0.9600 . ?
C00Q H00G 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
C00D S001 C00G 88.73(16) . . ?
C00A O003 C00P 116.1(3) . . ?
C00G N004 C009 109.7(3) . . ?
C00C C008 C00E 119.2(3) . . ?
C00C C008 C00F 121.8(3) . . ?
C00E C008 C00F 118.9(3) . . ?
N004 C009 C00A 121.0(3) . . ?
N004 C009 C00D 115.8(3) . . ?
C00D C009 C00A 123.2(3) . . ?
O002 C00A O003 125.4(3) . . ?
O002 C00A C009 122.6(3) . . ?
O003 C00A C009 111.9(3) . . ?
C00C C00B C00H 118.4(3) . . ?
C00K C00B C00C 122.8(3) . . ?
C00K C00B C00H 118.8(3) . . ?
C008 C00C C00B 122.0(3) . . ?
C008 C00C H00C 119.0 . . ?
C00B C00C H00C 119.0 . . ?
C009 C00D S001 109.5(2) . . ?
C009 C00D C00F 131.6(3) . . ?
C00F C00D S001 118.9(2) . . ?
C008 C00E H00E 120.0 . . ?
C00J C00E C008 120.0(3) . . ?
C00J C00E H00E 120.0 . . ?
O005 C00F C008 122.4(3) . . ?
O005 C00F C00D 118.3(3) . . ?
C008 C00F C00D 119.3(3) . . ?
N004 C00G S001 116.3(3) . . ?
N004 C00G C00L 122.3(4) . . ?
C00L C00G S001 121.3(3) . . ?
C00B C00H C00M 118.1(4) . . ?
C00J C00H C00B 118.2(3) . . ?
C00J C00H C00M 123.7(4) . . ?
C00E C00J C00H 122.2(3) . . ?
C00E C00J H00J 118.9 . . ?
C00H C00J H00J 118.9 . . ?
C00B C00K H00K 119.2 . . ?
C00N C00K C00B 121.7(4) . . ?
C00N C00K H00K 119.2 . . ?
F006 C00L C00G 111.4(4) . . ?
F007 C00L F006 102.4(4) . . ?
F007 C00L C00G 113.0(4) . . ?
F00I C00L F006 102.4(4) . . ?
F00I C00L F007 112.2(4) . . ?
F00I C00L C00G 114.3(4) . . ?
C00H C00M H00M 119.5 . . ?
C00O C00M C00H 120.9(4) . . ?
C00O C00M H00M 119.5 . . ?
C00K C00N H00N 120.6 . . ?
C00K C00N C00O 118.8(4) . . ?
C00O C00N H00N 120.6 . . ?
C00M C00O C00N 121.6(4) . . ?
C00M C00O H00O 119.2 . . ?
C00N C00O H00O 119.2 . . ?
O003 C00P H00A 109.9 . . ?
O003 C00P H00B 109.9 . . ?
H00A C00P H00B 108.3 . . ?
C00Q C00P O003 108.7(5) . . ?
C00Q C00P H00A 109.9 . . ?
C00Q C00P H00B 109.9 . . ?
C00P C00Q H00D 109.5 . . ?
C00P C00Q H00F 109.5 . . ?
C00P C00Q H00G 109.5 . . ?
H00D C00Q H00F 109.5 . . ?
H00D C00Q H00G 109.5 . . ?
H00F C00Q H00G 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
S001 C00D C00F O005 -53.7(4) . . . . ?
S001 C00D C00F C008 124.3(3) . . . . ?
S001 C00G C00L F006 -134.8(4) . . . . ?
S001 C00G C00L F007 110.6(5) . . . . ?
S001 C00G C00L F00I -19.4(6) . . . . ?
N004 C009 C00A O002 158.0(3) . . . . ?
N004 C009 C00A O003 -19.5(4) . . . . ?
N004 C009 C00D S001 -1.6(4) . . . . ?
N004 C009 C00D C00F -178.6(3) . . . . ?
N004 C00G C00L F006 47.5(6) . . . . ?
N004 C00G C00L F007 -67.1(6) . . . . ?
N004 C00G C00L F00I 163.0(4) . . . . ?
C008 C00E C00J C00H 2.3(6) . . . . ?
C009 N004 C00G S001 -0.3(4) . . . . ?
C009 N004 C00G C00L 177.5(4) . . . . ?
C009 C00D C00F O005 123.1(4) . . . . ?
C009 C00D C00F C008 -58.9(5) . . . . ?
C00A O003 C00P C00Q 87.1(5) . . . . ?
C00A C009 C00D S001 175.1(2) . . . . ?
C00A C009 C00D C00F -1.9(6) . . . . ?
C00B C00H C00J C00E -0.9(6) . . . . ?
C00B C00H C00M C00O -0.1(6) . . . . ?
C00B C00K C00N C00O 0.6(7) . . . . ?
C00C C008 C00E C00J -1.9(5) . . . . ?
C00C C008 C00F O005 165.8(3) . . . . ?
C00C C008 C00F C00D -12.1(5) . . . . ?
C00C C00B C00H C00J -1.0(5) . . . . ?
C00C C00B C00H C00M 179.1(3) . . . . ?
C00C C00B C00K C00N -179.3(4) . . . . ?
C00D S001 C00G N004 -0.5(3) . . . . ?
C00D S001 C00G C00L -178.3(3) . . . . ?
C00D C009 C00A O002 -18.6(5) . . . . ?
C00D C009 C00A O003 163.9(3) . . . . ?
C00E C008 C00C C00B 0.0(5) . . . . ?
C00E C008 C00F O005 -11.7(5) . . . . ?
C00E C008 C00F C00D 170.3(3) . . . . ?
C00F C008 C00C C00B -177.6(3) . . . . ?
C00F C008 C00E C00J 175.8(3) . . . . ?
C00G S001 C00D C009 1.1(3) . . . . ?
C00G S001 C00D C00F 178.6(3) . . . . ?
C00G N004 C009 C00A -175.5(3) . . . . ?
C00G N004 C009 C00D 1.2(4) . . . . ?
C00H C00B C00C C008 1.4(5) . . . . ?
C00H C00B C00K C00N 0.1(6) . . . . ?
C00H C00M C00O C00N 0.7(7) . . . . ?
C00J C00H C00M C00O 180.0(4) . . . . ?
C00K C00B C00C C008 -179.2(3) . . . . ?
C00K C00B C00H C00J 179.6(3) . . . . ?
C00K C00B C00H C00M -0.3(5) . . . . ?
C00K C00N C00O C00M -1.0(7) . . . . ?
C00M C00H C00J C00E 179.0(4) . . . . ?
C00P O003 C00A O002 1.4(6) . . . . ?
C00P O003 C00A C009 178.8(3) . . . . ?

_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 2.162
_oxdiff_exptl_absorpt_empirical_full_min 0.678
