# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_20200720-libs-an1209
_database_code_depnum_ccdc_archive 'CCDC 2042211'
_audit_update_record             
;
2020-11-03 deposited with the CCDC.	2021-03-31 downloaded from the CCDC.
;
_audit_creation_date             2020-07-20
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2018.07.26 svn.r3523 for OlexSys, GUI svn.r5532)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H10 F3 N O2 S'
_chemical_formula_sum            'C13 H10 F3 N O2 S'
_chemical_formula_weight         301.28
_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      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 1 2/m 1'
_space_group_name_Hall           '-C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   24.5740(14)
_cell_length_b                   6.8902(4)
_cell_length_c                   8.2777(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.150(5)
_cell_angle_gamma                90
_cell_volume                     1393.51(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3216
_cell_measurement_temperature    295(2)
_cell_measurement_theta_min      3.8590
_cell_measurement_theta_max      26.8070
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.266
_exptl_absorpt_correction_T_min  0.43468
_exptl_absorpt_correction_T_max  1.00000
_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            colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.3
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_unetI/netI     0.0205
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.918
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            10055
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.918
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.995
_diffrn_reflns_theta_min         3.874
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 16.0892
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.918
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1419
_reflns_number_total             1840
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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         0.470
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1840
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0587
_refine_ls_restrained_S_all      1.062
_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)+(0.0942P)²+1.2612P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1681
_refine_ls_wR_factor_ref         0.1851
_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. Others
 Fixed Sof: H00A(0.5) H00B(0.5) H00E(0.5) H00F(0.5) H00G(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C00A(H00A,H00B)
3.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00C(H00C), C00D(H00D)
3.c Idealised Me refined as rotating group:
 C00E(H00E,H00F,H00G)
;
_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 0.67258(4) 0.5000 0.95310(10) 0.0550(3) Uani 1 2 d S T P . .
O002 O 0.85227(12) 0.5000 0.8608(4) 0.0778(8) Uani 1 2 d S T P . .
O003 O 0.86481(12) 0.5000 1.1327(4) 0.0762(8) Uani 1 2 d S T P . .
N004 N 0.75739(13) 0.5000 1.1608(3) 0.0564(7) Uani 1 2 d S T P . .
C005 C 0.68657(13) 0.5000 0.5957(4) 0.0492(7) Uani 1 2 d S T P . .
C006 C 0.73516(13) 0.5000 0.8803(4) 0.0470(7) Uani 1 2 d S T P . .
C007 C 0.77534(14) 0.5000 1.0086(4) 0.0483(7) Uani 1 2 d S T P . .
C008 C 0.83411(15) 0.5000 0.9897(5) 0.0570(8) Uani 1 2 d S T P . .
C009 C 0.66181(12) 0.3271(4) 0.5450(3) 0.0642(7) Uani 1 1 d . . . . .
H009 H 0.6780 0.2098 0.5788 0.077 Uiso 1 1 calc R . . . .
C00A C 0.74074(14) 0.5000 0.7015(4) 0.0574(8) Uani 1 2 d S T P . .
H00A H 0.7614 0.3863 0.6757 0.069 Uiso 0.5 1 calc R . . . .
H00B H 0.7614 0.6137 0.6757 0.069 Uiso 0.5 1 calc R . . . .
C00B C 0.58901(17) 0.5000 0.3938(5) 0.0772(12) Uani 1 2 d S T P . .
C00C C 0.61311(13) 0.3278(5) 0.4441(3) 0.0779(8) Uani 1 1 d . . . . .
H00C H 0.5967 0.2110 0.4103 0.093 Uiso 1 1 calc R . . . .
C00D C 0.70451(16) 0.5000 1.1473(4) 0.0603(9) Uani 1 2 d S T P . .
H00D H 0.6850 0.5000 1.2376 0.072 Uiso 1 2 calc RS T P . .
C00E C 0.9228(2) 0.5000 1.1248(8) 0.120(2) Uani 1 2 d S T P . .
H00E H 0.9344 0.3727 1.0960 0.180 Uiso 0.5 1 calc GR . . A -1
H00F H 0.9412 0.5356 1.2288 0.180 Uiso 0.5 1 calc GR . . A -1
H00G H 0.9317 0.5917 1.0443 0.180 Uiso 0.5 1 calc GR . . A -1
F1 F 0.5485(2) 0.5000 0.1317(5) 0.260(5) Uani 1 2 d S T P . .
F2 F 0.50743(15) 0.3602(8) 0.2903(6) 0.264(3) Uani 1 1 d . . . . .
C3 C 0.5392(2) 0.5000 0.2758(8) 0.125(3) Uani 1 2 d S T P . .


_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 C006 1.711(3) . ?
S001 C00D 1.712(4) . ?
O002 C008 1.201(5) . ?
O003 C008 1.333(4) . ?
O003 C00E 1.434(6) . ?
N004 C007 1.379(4) . ?
N004 C00D 1.292(5) . ?
C005 C009 1.382(3) 6_565 ?
C005 C009 1.382(3) . ?
C005 C00A 1.513(5) . ?
C006 C007 1.370(4) . ?
C006 C00A 1.501(4) . ?
C007 C008 1.469(5) . ?
C009 H009 0.9300 . ?
C009 C00C 1.384(4) . ?
C00A H00A 0.9700 . ?
C00A H00B 0.9700 . ?
C00B C00C 1.371(4) 6_565 ?
C00B C00C 1.371(4) . ?
C00B C3 1.482(7) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9600 . ?
C00E H00F 0.9600 . ?
C00E H00G 0.9600 . ?
F1 C3 1.238(8) . ?
F2 C3 1.254(5) . ?
C3 F2 1.254(5) 6_565 ?

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
C006 S001 C00D 89.54(17) . . ?
C008 O003 C00E 115.5(4) . . ?
C00D N004 C007 109.8(3) . . ?
C009 C005 C009 119.0(3) 6_565 . ?
C009 C005 C00A 120.47(16) 6_565 . ?
C009 C005 C00A 120.47(16) . . ?
C007 C006 S001 109.1(2) . . ?
C007 C006 C00A 129.0(3) . . ?
C00A C006 S001 121.9(2) . . ?
N004 C007 C008 120.8(3) . . ?
C006 C007 N004 115.7(3) . . ?
C006 C007 C008 123.6(3) . . ?
O002 C008 O003 124.1(4) . . ?
O002 C008 C007 123.9(3) . . ?
O003 C008 C007 112.0(3) . . ?
C005 C009 H009 119.9 . . ?
C005 C009 C00C 120.3(3) . . ?
C00C C009 H009 119.9 . . ?
C005 C00A H00A 108.8 . . ?
C005 C00A H00B 108.8 . . ?
C006 C00A C005 113.8(3) . . ?
C006 C00A H00A 108.8 . . ?
C006 C00A H00B 108.8 . . ?
H00A C00A H00B 107.7 . . ?
C00C C00B C00C 119.9(4) . 6_565 ?
C00C C00B C3 119.98(19) 6_565 . ?
C00C C00B C3 119.98(19) . . ?
C009 C00C H00C 119.9 . . ?
C00B C00C C009 120.2(3) . . ?
C00B C00C H00C 119.9 . . ?
S001 C00D H00D 122.1 . . ?
N004 C00D S001 115.9(3) . . ?
N004 C00D H00D 122.1 . . ?
O003 C00E H00E 109.5 . . ?
O003 C00E H00F 109.5 . . ?
O003 C00E H00G 109.5 . . ?
H00E C00E H00F 109.5 . . ?
H00E C00E H00G 109.5 . . ?
H00F C00E H00G 109.5 . . ?
F1 C3 C00B 114.2(5) . . ?
F1 C3 F2 105.9(5) . 6_565 ?
F1 C3 F2 105.9(5) . . ?
F2 C3 C00B 114.6(4) . . ?
F2 C3 C00B 114.6(4) 6_565 . ?
F2 C3 F2 100.4(7) 6_565 . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'
