# Electronic Supplementary Material (ESI) for Green Chemistry.
# 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_1023-1
_database_code_depnum_ccdc_archive 'CCDC 2243485'
loop_
_audit_author_name
_audit_author_address
chuxueqiang
;Nanjing Tech University
China
;
_audit_update_record             
;
2023-02-21 deposited with the CCDC.	2023-11-08 downloaded from the CCDC.
;
_audit_creation_date             2023-02-20
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H8 F7 N3'
_chemical_formula_sum            'C13 H8 F7 N3'
_chemical_formula_weight         339.22
_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'

_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                   11.5372(11)
_cell_length_b                   11.7335(9)
_cell_length_c                   10.3893(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.132(9)
_cell_angle_gamma                90
_cell_volume                     1363.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2802
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      28.2740
_cell_measurement_theta_min      2.6640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.168
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.60147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             680
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5493
_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         2.515
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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     -9.00  77.00   1.00    2.50    --   12.05  38.00-120.00   86
  2  ω    -57.00  39.00   1.00    2.50    --   12.05 -57.00  60.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0139191000
_diffrn_orient_matrix_UB_12      0.0556314000
_diffrn_orient_matrix_UB_13      -0.0179349000
_diffrn_orient_matrix_UB_21      -0.0463054000
_diffrn_orient_matrix_UB_22      -0.0034920000
_diffrn_orient_matrix_UB_23      -0.0591042000
_diffrn_orient_matrix_UB_31      -0.0410781000
_diffrn_orient_matrix_UB_32      0.0229764000
_diffrn_orient_matrix_UB_33      0.0340383000
_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                1991
_reflns_number_total             2399
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.280
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       0.017(2)
_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   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.069
_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)+(0.0560P)²+0.0775P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C8(H8)
;
_atom_sites_solution_hydrogens   mixed
_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
F1 F -0.01698(10) 0.49150(10) 0.78203(11) 0.0483(3) Uani 1 1 d . . . . .
F2 F 0.04930(10) 0.62780(8) 0.67885(10) 0.0454(3) Uani 1 1 d . . . . .
F3 F 0.18691(12) 0.47815(10) 0.96466(11) 0.0605(4) Uani 1 1 d . . . . .
F4 F 0.27376(10) 0.59982(11) 0.85918(13) 0.0619(4) Uani 1 1 d . . . . .
F5 F 0.02269(12) 0.64891(10) 0.98081(13) 0.0628(4) Uani 1 1 d . . . . .
F6 F 0.20775(14) 0.68172(13) 1.07520(14) 0.0879(5) Uani 1 1 d . . . . .
F7 F 0.12546(11) 0.76416(9) 0.89356(12) 0.0593(4) Uani 1 1 d . . . . .
N1 N 0.56039(16) 0.65288(13) 0.08559(16) 0.0467(4) Uani 1 1 d . . . . .
N2 N 0.25497(16) 0.30519(13) 0.51871(17) 0.0377(4) Uani 1 1 d . . . . .
H2A H 0.217(2) 0.2779(18) 0.576(2) 0.055(6) Uiso 1 1 d . . . . .
H2B H 0.3011(18) 0.2658(17) 0.4795(19) 0.044(6) Uiso 1 1 d . . . . .
N3 N 0.13184(15) 0.33768(12) 0.70635(16) 0.0396(4) Uani 1 1 d . . . . .
H3 H 0.0876(18) 0.3264(16) 0.764(2) 0.048(6) Uiso 1 1 d . . . . .
C1 C 0.33201(16) 0.41126(14) 0.30512(16) 0.0327(4) Uani 1 1 d . . . . .
H1 H 0.296497 0.338144 0.286562 0.039 Uiso 1 1 calc R U . . .
C2 C 0.39560(16) 0.45681(14) 0.22114(17) 0.0342(4) Uani 1 1 d . . . . .
H2 H 0.404808 0.414758 0.146129 0.041 Uiso 1 1 calc R U . . .
C3 C 0.44611(15) 0.56426(14) 0.24642(16) 0.0305(4) Uani 1 1 d . . . . .
C4 C 0.43207(15) 0.62546(14) 0.35601(17) 0.0321(4) Uani 1 1 d . . . . .
H4 H 0.465167 0.699718 0.372519 0.038 Uiso 1 1 calc R U . . .
C5 C 0.37036(15) 0.57864(13) 0.44046(16) 0.0306(4) Uani 1 1 d . . . . .
H5 H 0.362491 0.620367 0.516225 0.037 Uiso 1 1 calc R U . . .
C6 C 0.31898(14) 0.47052(13) 0.41659(16) 0.0278(4) Uani 1 1 d . . . . .
C7 C 0.25431(15) 0.41946(14) 0.51005(16) 0.0292(4) Uani 1 1 d . . . . .
C8 C 0.19718(16) 0.48610(14) 0.58268(17) 0.0321(4) Uani 1 1 d . . . . .
H8 H 0.197098 0.566126 0.568772 0.038 Uiso 1 1 calc R U . . .
C9 C 0.13749(15) 0.44397(14) 0.67815(16) 0.0310(4) Uani 1 1 d . . . . .
C10 C 0.08270(15) 0.53296(14) 0.75227(17) 0.0332(4) Uani 1 1 d . . . . .
C11 C 0.16810(17) 0.56947(16) 0.88357(18) 0.0404(5) Uani 1 1 d . . . . .
C12 C 0.1293(2) 0.66762(17) 0.9597(2) 0.0495(5) Uani 1 1 d . . . . .
C13 C 0.51059(17) 0.61292(15) 0.15718(17) 0.0353(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
F1 C10 1.3522(19) . ?
F2 C10 1.3510(19) . ?
F3 C11 1.347(2) . ?
F4 C11 1.352(2) . ?
F5 C12 1.319(2) . ?
F6 C12 1.325(2) . ?
F7 C12 1.320(2) . ?
N1 C13 1.145(2) . ?
N2 H2A 0.88(2) . ?
N2 H2B 0.88(2) . ?
N2 C7 1.344(2) . ?
N3 H3 0.89(2) . ?
N3 C9 1.286(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.378(2) . ?
C1 C6 1.390(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.387(2) . ?
C3 C4 1.389(2) . ?
C3 C13 1.441(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.372(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.397(2) . ?
C6 C7 1.487(2) . ?
C7 C8 1.363(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.427(2) . ?
C9 C10 1.523(2) . ?
C10 C11 1.536(3) . ?
C11 C12 1.525(3) . ?

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
H2A N2 H2B 125.5(19) . . ?
C7 N2 H2A 114.4(14) . . ?
C7 N2 H2B 119.2(13) . . ?
C9 N3 H3 111.6(13) . . ?
C2 C1 H1 119.5 . . ?
C2 C1 C6 121.08(16) . . ?
C6 C1 H1 119.5 . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.80(16) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 C4 119.84(15) . . ?
C2 C3 C13 119.84(15) . . ?
C4 C3 C13 120.30(15) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 C3 119.99(15) . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.93(15) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 C5 118.34(15) . . ?
C1 C6 C7 121.06(15) . . ?
C5 C6 C7 120.58(14) . . ?
N2 C7 C6 116.75(14) . . ?
N2 C7 C8 122.07(15) . . ?
C8 C7 C6 121.18(15) . . ?
C7 C8 H8 117.7 . . ?
C7 C8 C9 124.52(15) . . ?
C9 C8 H8 117.7 . . ?
N3 C9 C8 123.65(16) . . ?
N3 C9 C10 119.94(15) . . ?
C8 C9 C10 116.37(14) . . ?
F1 C10 C9 110.49(14) . . ?
F1 C10 C11 107.11(14) . . ?
F2 C10 F1 106.51(14) . . ?
F2 C10 C9 112.06(13) . . ?
F2 C10 C11 107.73(14) . . ?
C9 C10 C11 112.63(14) . . ?
F3 C11 F4 108.16(15) . . ?
F3 C11 C10 107.70(15) . . ?
F3 C11 C12 107.39(16) . . ?
F4 C11 C10 108.61(15) . . ?
F4 C11 C12 106.91(16) . . ?
C12 C11 C10 117.74(16) . . ?
F5 C12 F6 109.23(18) . . ?
F5 C12 F7 108.40(16) . . ?
F5 C12 C11 111.36(17) . . ?
F6 C12 C11 109.97(17) . . ?
F7 C12 F6 107.02(18) . . ?
F7 C12 C11 110.74(17) . . ?
N1 C13 C3 178.9(2) . . ?

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
F1 C10 C11 F3 56.52(18) . . . . ?
F1 C10 C11 F4 173.43(13) . . . . ?
F1 C10 C11 C12 -65.0(2) . . . . ?
F2 C10 C11 F3 170.76(13) . . . . ?
F2 C10 C11 F4 -72.33(17) . . . . ?
F2 C10 C11 C12 49.3(2) . . . . ?
F3 C11 C12 F5 -68.2(2) . . . . ?
F3 C11 C12 F6 53.1(2) . . . . ?
F3 C11 C12 F7 171.14(16) . . . . ?
F4 C11 C12 F5 175.96(16) . . . . ?
F4 C11 C12 F6 -62.8(2) . . . . ?
F4 C11 C12 F7 55.3(2) . . . . ?
N2 C7 C8 C9 2.8(3) . . . . ?
N3 C9 C10 F1 -34.5(2) . . . . ?
N3 C9 C10 F2 -153.13(16) . . . . ?
N3 C9 C10 C11 85.2(2) . . . . ?
C1 C2 C3 C4 -0.2(3) . . . . ?
C1 C2 C3 C13 -178.76(16) . . . . ?
C1 C6 C7 N2 28.0(2) . . . . ?
C1 C6 C7 C8 -151.87(17) . . . . ?
C2 C1 C6 C5 1.0(3) . . . . ?
C2 C1 C6 C7 -177.63(15) . . . . ?
C2 C3 C4 C5 1.3(3) . . . . ?
C3 C4 C5 C6 -1.3(3) . . . . ?
C4 C5 C6 C1 0.1(2) . . . . ?
C4 C5 C6 C7 178.78(15) . . . . ?
C5 C6 C7 N2 -150.68(16) . . . . ?
C5 C6 C7 C8 29.5(2) . . . . ?
C6 C1 C2 C3 -1.0(3) . . . . ?
C6 C7 C8 C9 -177.33(16) . . . . ?
C7 C8 C9 N3 0.4(3) . . . . ?
C7 C8 C9 C10 177.97(16) . . . . ?
C8 C9 C10 F1 147.76(15) . . . . ?
C8 C9 C10 F2 29.2(2) . . . . ?
C8 C9 C10 C11 -92.50(18) . . . . ?
C9 C10 C11 F3 -65.16(19) . . . . ?
C9 C10 C11 F4 51.76(19) . . . . ?
C9 C10 C11 C12 173.35(16) . . . . ?
C10 C11 C12 F5 53.5(2) . . . . ?
C10 C11 C12 F6 174.71(17) . . . . ?
C10 C11 C12 F7 -67.2(2) . . . . ?
C13 C3 C4 C5 179.88(16) . . . . ?

_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 1.336
_oxdiff_exptl_absorpt_empirical_full_min 0.736
####################################################################### 
# 
# 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_3004
_database_code_depnum_ccdc_archive 'CCDC 2280088'
loop_
_audit_author_name
_audit_author_address
xueqiang
;Nanjing Tech university
China
;
_audit_update_record             
;
2023-07-07 deposited with the CCDC.	2023-11-08 downloaded from the CCDC.
;
_audit_creation_date             2023-07-07
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 F7 N O3 S'
_chemical_formula_sum            'C19 H14 F7 N O3 S'
_chemical_formula_weight         469.37
_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      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                   6.2755(10)
_cell_length_b                   8.1410(9)
_cell_length_c                   19.0094(12)
_cell_angle_alpha                81.051(7)
_cell_angle_beta                 85.123(9)
_cell_angle_gamma                84.276(11)
_cell_volume                     952.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3018
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.2190
_cell_measurement_theta_min      4.6970
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.365
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18357
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light colourless'
_exptl_crystal_density_diffrn    1.637
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             476
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0882
_diffrn_reflns_av_unetI/netI     0.0801
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            5808
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.599
_diffrn_reflns_theta_max         66.599
_diffrn_reflns_theta_min         2.359
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  30.00   1.00    1.00    --  -40.73  38.00  30.00   93
  2  ω    -72.00  23.00   1.00    1.00    --  -40.73  77.00 120.00   95
  3  ω     33.00  76.00   1.00    1.00    --   40.73-125.00 -90.00   43
  4  ω     59.00  85.00   1.00    1.00    --   40.73-125.00   0.00   26
  5  ω     52.00 120.00   1.00    1.00    --  106.95 -45.00 120.00   68
  6  ω     83.00 178.00   1.00    1.00    --  106.95  30.00  60.00   95
  7  ω    151.00 177.00   1.00    1.00    --  106.95 125.00 -30.00   26
  8  ω    114.00 155.00   1.00    1.00    --  106.95 125.00 -90.00   41
  9  ω     99.00 130.00   1.00    1.00    --  106.95 125.00 -30.00   31
 10  ω     95.00 165.00   1.00    1.00    --  106.95 125.00  60.00   70
 11  ω    100.00 172.00   1.00    1.00    --  106.95  30.00 -30.00   72
 12  ω     82.00 133.00   1.00    1.00    --  106.95 -45.00-120.00   51
 13  ω     79.00 109.00   1.00    1.00    --  106.95 -95.00 -60.00   30
 14  ω     44.00 108.00   1.00    1.00    --  106.95 -95.00  30.00   64
 15  ω     60.00 103.00   1.00    1.00    --  106.95 -95.00 120.00   43
 16  ω     47.00 130.00   1.00    1.00    --  106.95 -45.00   0.00   83
 17  ω     41.00 121.00   1.00    1.00    --  106.95-125.00 -60.00   80
 18  ω   -115.00 -16.00   1.00    1.00    --  -40.73 -38.00-150.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1955539000
_diffrn_orient_matrix_UB_12      -0.0722113000
_diffrn_orient_matrix_UB_13      0.0442336000
_diffrn_orient_matrix_UB_21      -0.1098218000
_diffrn_orient_matrix_UB_22      0.1778479000
_diffrn_orient_matrix_UB_23      0.0001700000
_diffrn_orient_matrix_UB_31      -0.1042735000
_diffrn_orient_matrix_UB_32      -0.0117916000
_diffrn_orient_matrix_UB_33      -0.0693388000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2707
_reflns_number_total             3370
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.906
_refine_diff_density_min         -1.187
_refine_diff_density_rms         0.171
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0955
_refine_ls_restrained_S_all      1.087
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2680
_refine_ls_wR_factor_ref         0.2865
_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), C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C14(H14), C15(H15),
 C17(H17), C18(H18)
2.b Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C)
;
_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
S1 S 0.69093(15) 0.68784(10) 0.10706(4) 0.0197(4) Uani 1 1 d . . . . .
O1 O 0.4146(5) 0.3812(4) 0.26644(15) 0.0316(8) Uani 1 1 d . . . . .
F2 F 0.4797(5) 0.1306(3) 0.37105(13) 0.0370(7) Uani 1 1 d . . . . .
F3 F 0.6720(4) 0.2778(3) 0.42314(14) 0.0391(7) Uani 1 1 d . . . . .
F4 F 0.3215(5) 0.4906(3) 0.44752(14) 0.0458(8) Uani 1 1 d . . . . .
F5 F 0.1256(4) 0.3455(4) 0.39539(14) 0.0452(8) Uani 1 1 d . . . . .
F6 F 0.2263(6) 0.0726(4) 0.49433(17) 0.0632(10) Uani 1 1 d . . . . .
F7 F 0.4140(6) 0.2159(5) 0.54578(15) 0.0623(10) Uani 1 1 d . . . . .
F8 F 0.0787(6) 0.2883(5) 0.53752(17) 0.0704(12) Uani 1 1 d . . . . .
O3 O 0.8143(5) 0.8298(3) 0.10000(13) 0.0271(7) Uani 1 1 d . . . . .
O2 O 0.5097(5) 0.6895(3) 0.06668(13) 0.0255(7) Uani 1 1 d . . . . .
N1 N 0.5881(5) 0.6521(4) 0.19270(16) 0.0224(7) Uani 1 1 d . . . . .
H1 H 0.452697 0.630275 0.199219 0.027 Uiso 1 1 calc R U . . .
C1 C 0.8325(7) 0.7908(5) 0.25680(19) 0.0223(9) Uani 1 1 d . . . . .
C2 C 0.7575(7) 0.9535(5) 0.2349(2) 0.0243(9) Uani 1 1 d . . . . .
H2 H 0.624330 0.979066 0.213613 0.029 Uiso 1 1 calc R U . . .
C3 C 0.8816(8) 1.0809(5) 0.2447(2) 0.0316(10) Uani 1 1 d . . . . .
H3 H 0.831703 1.194239 0.230204 0.038 Uiso 1 1 calc R U . . .
C4 C 1.0761(8) 1.0430(6) 0.2751(2) 0.0341(11) Uani 1 1 d . . . . .
H4 H 1.159058 1.130588 0.281202 0.041 Uiso 1 1 calc R U . . .
C5 C 1.1514(8) 0.8783(6) 0.2970(2) 0.0367(11) Uani 1 1 d . . . . .
H5 H 1.285891 0.852524 0.317455 0.044 Uiso 1 1 calc R U . . .
C6 C 1.0260(7) 0.7503(5) 0.2884(2) 0.0306(10) Uani 1 1 d . . . . .
H6 H 1.073134 0.637011 0.303988 0.037 Uiso 1 1 calc R U . . .
C7 C 0.6923(6) 0.6535(5) 0.25285(19) 0.0214(8) Uani 1 1 d . . . . .
C8 C 0.6564(7) 0.5374(5) 0.3126(2) 0.0253(9) Uani 1 1 d . . . . .
H8 H 0.724643 0.545434 0.354541 0.030 Uiso 1 1 calc R U . . .
C9 C 0.5213(7) 0.4056(5) 0.31427(19) 0.0237(9) Uani 1 1 d . . . . .
C10 C 0.4970(7) 0.2838(5) 0.3855(2) 0.0254(9) Uani 1 1 d . . . . .
C11 C 0.2991(7) 0.3376(5) 0.4324(2) 0.0286(10) Uani 1 1 d . . . . .
C12 C 0.2537(9) 0.2241(6) 0.5044(2) 0.0407(12) Uani 1 1 d . . . . .
C13 C 0.8621(6) 0.5078(5) 0.09798(18) 0.0194(8) Uani 1 1 d . . . . .
C14 C 0.7920(7) 0.3845(5) 0.06425(19) 0.0228(9) Uani 1 1 d . . . . .
H14 H 0.654871 0.398632 0.045341 0.027 Uiso 1 1 calc R U . . .
C15 C 0.9285(7) 0.2399(5) 0.0590(2) 0.0257(9) Uani 1 1 d . . . . .
H15 H 0.883517 0.154806 0.036121 0.031 Uiso 1 1 calc R U . . .
C16 C 1.1296(7) 0.2181(5) 0.08683(19) 0.0233(9) Uani 1 1 d . . . . .
C17 C 1.1944(7) 0.3445(5) 0.1192(2) 0.0266(9) Uani 1 1 d . . . . .
H17 H 1.331536 0.330633 0.138007 0.032 Uiso 1 1 calc R U . . .
C18 C 1.0633(6) 0.4915(5) 0.1247(2) 0.0236(8) Uani 1 1 d . . . . .
H18 H 1.110608 0.577990 0.146222 0.028 Uiso 1 1 calc R U . . .
C19 C 1.2712(7) 0.0590(5) 0.0840(2) 0.0316(10) Uani 1 1 d . . . . .
H19A H 1.223812 -0.026653 0.122654 0.047 Uiso 1 1 calc R U . . .
H19B H 1.419989 0.078758 0.089416 0.047 Uiso 1 1 calc R U . . .
H19C H 1.262101 0.021076 0.037924 0.047 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 O3 1.437(3) . ?
S1 O2 1.423(3) . ?
S1 N1 1.692(3) . ?
S1 C13 1.751(4) . ?
O1 C9 1.225(5) . ?
F2 C10 1.335(5) . ?
F3 C10 1.353(5) . ?
F4 C11 1.345(5) . ?
F5 C11 1.337(5) . ?
F6 C12 1.307(6) . ?
F7 C12 1.319(6) . ?
F8 C12 1.322(6) . ?
N1 H1 0.8800 . ?
N1 C7 1.367(5) . ?
C1 C2 1.374(5) . ?
C1 C6 1.387(6) . ?
C1 C7 1.504(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.401(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.382(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.389(7) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(6) . ?
C6 H6 0.9500 . ?
C7 C8 1.378(5) . ?
C8 H8 0.9500 . ?
C8 C9 1.428(6) . ?
C9 C10 1.555(5) . ?
C10 C11 1.534(6) . ?
C11 C12 1.549(6) . ?
C13 C14 1.396(5) . ?
C13 C18 1.387(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.397(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.394(6) . ?
C16 C17 1.387(6) . ?
C16 C19 1.501(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.396(6) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
O3 S1 N1 107.66(16) . . ?
O3 S1 C13 109.78(18) . . ?
O2 S1 O3 121.49(17) . . ?
O2 S1 N1 103.57(17) . . ?
O2 S1 C13 109.22(17) . . ?
N1 S1 C13 103.47(16) . . ?
S1 N1 H1 116.4 . . ?
C7 N1 S1 127.1(3) . . ?
C7 N1 H1 116.4 . . ?
C2 C1 C6 121.7(4) . . ?
C2 C1 C7 119.2(4) . . ?
C6 C1 C7 118.8(3) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.6(4) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(4) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.7 . . ?
C3 C4 C5 120.7(4) . . ?
C5 C4 H4 119.7 . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 119.0(4) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 119.5(4) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
N1 C7 C1 120.3(3) . . ?
N1 C7 C8 120.5(4) . . ?
C8 C7 C1 119.1(3) . . ?
C7 C8 H8 118.6 . . ?
C7 C8 C9 122.9(3) . . ?
C9 C8 H8 118.6 . . ?
O1 C9 C8 127.1(3) . . ?
O1 C9 C10 115.8(4) . . ?
C8 C9 C10 117.0(3) . . ?
F2 C10 F3 108.1(3) . . ?
F2 C10 C9 109.2(3) . . ?
F2 C10 C11 109.3(4) . . ?
F3 C10 C9 110.5(3) . . ?
F3 C10 C11 108.1(3) . . ?
C11 C10 C9 111.6(3) . . ?
F4 C11 C10 108.4(4) . . ?
F4 C11 C12 107.1(4) . . ?
F5 C11 F4 108.8(3) . . ?
F5 C11 C10 108.5(3) . . ?
F5 C11 C12 107.1(4) . . ?
C10 C11 C12 116.7(4) . . ?
F6 C12 F7 108.3(4) . . ?
F6 C12 F8 109.5(5) . . ?
F6 C12 C11 111.1(4) . . ?
F7 C12 F8 108.2(4) . . ?
F7 C12 C11 111.0(4) . . ?
F8 C12 C11 108.7(4) . . ?
C14 C13 S1 119.0(3) . . ?
C18 C13 S1 119.1(3) . . ?
C18 C13 C14 121.9(3) . . ?
C13 C14 H14 120.9 . . ?
C13 C14 C15 118.3(4) . . ?
C15 C14 H14 120.9 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(4) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C19 120.8(4) . . ?
C17 C16 C15 118.7(3) . . ?
C17 C16 C19 120.4(4) . . ?
C16 C17 H17 119.1 . . ?
C16 C17 C18 121.7(4) . . ?
C18 C17 H17 119.1 . . ?
C13 C18 C17 118.1(4) . . ?
C13 C18 H18 120.9 . . ?
C17 C18 H18 120.9 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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
S1 N1 C7 C1 44.7(5) . . . . ?
S1 N1 C7 C8 -140.6(3) . . . . ?
S1 C13 C14 C15 -178.4(3) . . . . ?
S1 C13 C18 C17 177.8(3) . . . . ?
O1 C9 C10 F2 37.8(5) . . . . ?
O1 C9 C10 F3 156.5(4) . . . . ?
O1 C9 C10 C11 -83.2(5) . . . . ?
F2 C10 C11 F4 178.8(3) . . . . ?
F2 C10 C11 F5 -63.2(4) . . . . ?
F2 C10 C11 C12 57.8(5) . . . . ?
F3 C10 C11 F4 61.4(4) . . . . ?
F3 C10 C11 F5 179.4(3) . . . . ?
F3 C10 C11 C12 -59.6(5) . . . . ?
F4 C11 C12 F6 179.0(4) . . . . ?
F4 C11 C12 F7 -60.5(5) . . . . ?
F4 C11 C12 F8 58.4(5) . . . . ?
F5 C11 C12 F6 62.5(5) . . . . ?
F5 C11 C12 F7 -177.0(4) . . . . ?
F5 C11 C12 F8 -58.1(5) . . . . ?
O3 S1 N1 C7 -43.9(4) . . . . ?
O3 S1 C13 C14 -144.6(3) . . . . ?
O3 S1 C13 C18 35.6(3) . . . . ?
O2 S1 N1 C7 -173.8(3) . . . . ?
O2 S1 C13 C14 -9.1(4) . . . . ?
O2 S1 C13 C18 171.1(3) . . . . ?
N1 S1 C13 C14 100.7(3) . . . . ?
N1 S1 C13 C18 -79.0(3) . . . . ?
N1 C7 C8 C9 3.6(6) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C1 C7 C8 C9 178.3(4) . . . . ?
C2 C1 C6 C5 -1.3(6) . . . . ?
C2 C1 C7 N1 46.3(5) . . . . ?
C2 C1 C7 C8 -128.4(4) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 -0.7(7) . . . . ?
C4 C5 C6 C1 1.5(6) . . . . ?
C6 C1 C2 C3 0.3(6) . . . . ?
C6 C1 C7 N1 -139.4(4) . . . . ?
C6 C1 C7 C8 45.9(5) . . . . ?
C7 C1 C2 C3 174.5(3) . . . . ?
C7 C1 C6 C5 -175.5(4) . . . . ?
C7 C8 C9 O1 -3.4(7) . . . . ?
C7 C8 C9 C10 179.8(4) . . . . ?
C8 C9 C10 F2 -145.0(4) . . . . ?
C8 C9 C10 F3 -26.3(5) . . . . ?
C8 C9 C10 C11 94.0(5) . . . . ?
C9 C10 C11 F4 -60.4(4) . . . . ?
C9 C10 C11 F5 57.6(4) . . . . ?
C9 C10 C11 C12 178.7(4) . . . . ?
C10 C11 C12 F6 -59.3(6) . . . . ?
C10 C11 C12 F7 61.2(6) . . . . ?
C10 C11 C12 F8 -179.9(4) . . . . ?
C13 S1 N1 C7 72.3(4) . . . . ?
C13 C14 C15 C16 0.2(6) . . . . ?
C14 C13 C18 C17 -2.0(6) . . . . ?
C14 C15 C16 C17 -1.0(6) . . . . ?
C14 C15 C16 C19 177.2(4) . . . . ?
C15 C16 C17 C18 0.3(6) . . . . ?
C16 C17 C18 C13 1.1(6) . . . . ?
C18 C13 C14 C15 1.3(6) . . . . ?
C19 C16 C17 C18 -177.9(4) . . . . ?

_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 3.707
_oxdiff_exptl_absorpt_empirical_full_min 0.312
