# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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. 
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data_yrx-74c
_database_code_depnum_ccdc_archive 'CCDC 1830626'
_audit_update_record             
;
2018-03-18 deposited with the CCDC.
2018-10-24 downloaded from the CCDC.
;
_audit_creation_date             2018-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H9 Cl F3 N O3 S'
_chemical_formula_sum            'C16 H9 Cl F3 N O3 S'
_chemical_formula_weight         387.75
_chemical_absolute_configuration ?
_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'
Cl Cl 0.1484 0.1585 '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      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'
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+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'x+1, -y+1, z+1/2'
'-x+1, y+1, z+1/2'

_cell_length_a                   15.569(2)
_cell_length_b                   29.973(4)
_cell_length_c                   7.0564(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3292.9(8)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    2015
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.488
_cell_measurement_theta_min      2.949
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_correction_T_min  0.907
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0474
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4604
_diffrn_reflns_point_group_measured_fraction_full 0.884
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.488
_diffrn_reflns_theta_max         25.488
_diffrn_reflns_theta_min         2.949
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.609
_reflns_Friedel_fraction_full    0.747
_reflns_Friedel_fraction_max     0.747
_reflns_number_gt                1721
_reflns_number_total             2015
_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         0.440
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.138
_refine_ls_abs_structure_details 
;
 Flack x determined using 584 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.115
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         2015
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0494
_refine_ls_restrained_S_all      1.115
_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)+(0.0730P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1180
_refine_ls_wR_factor_ref         0.1234
_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:
 C8(H8), C12(H12), C3(H3), C10(H10), C5(H5), C13(H13), C16(H16), C14(H14),
 C15(H15)
;
_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
Cl1 Cl 0.74890(8) 0.21911(5) 0.6196(3) 0.0530(5) Uani 1 1 d . . . . .
S1 S 0.68851(10) 0.11323(5) 0.4672(3) 0.0573(5) Uani 1 1 d . . . . .
O2 O 0.6754(3) 0.13867(18) 0.3017(6) 0.0687(14) Uani 1 1 d . . . . .
O1 O 0.6471(3) 0.13693(13) 0.6428(6) 0.0531(11) Uani 1 1 d . . . . .
O3 O 0.7690(3) 0.09656(18) 0.5235(8) 0.0802(16) Uani 1 1 d . . . . .
N1 N 0.4440(3) 0.28891(16) 0.6059(8) 0.0499(12) Uani 1 1 d . . . . .
C7 C 0.5883(3) 0.25675(18) 0.6104(9) 0.0396(13) Uani 1 1 d . . . . .
F1 F 0.5384(3) 0.07688(17) 0.4173(11) 0.1161(19) Uani 1 1 d . . . . .
C8 C 0.6223(3) 0.29990(18) 0.6064(9) 0.0421(13) Uani 1 1 d . . . . .
H8 H 0.681600 0.303820 0.607338 0.050 Uiso 1 1 calc R . . . .
C6 C 0.4964(3) 0.25212(17) 0.6097(9) 0.0405(13) Uani 1 1 d . . . . .
C11 C 0.6021(4) 0.38288(19) 0.5955(9) 0.0462(14) Uani 1 1 d . . . . .
C9 C 0.5694(3) 0.33668(18) 0.6010(8) 0.0421(13) Uani 1 1 d . . . . .
C12 C 0.6728(4) 0.3936(2) 0.4871(12) 0.0613(17) Uani 1 1 d . . . . .
H12 H 0.699951 0.371572 0.416158 0.074 Uiso 1 1 calc R . . . .
C4 C 0.6376(3) 0.21698(18) 0.6176(10) 0.0397(12) Uani 1 1 d . . . . .
F3 F 0.6438(5) 0.0382(2) 0.3225(13) 0.168(4) Uani 1 1 d . . . . .
C2 C 0.5973(4) 0.17660(19) 0.6221(9) 0.0455(13) Uani 1 1 d . . . . .
F2 F 0.6164(5) 0.04317(19) 0.6144(12) 0.145(3) Uani 1 1 d . . . . .
C3 C 0.5077(4) 0.1726(2) 0.6225(9) 0.0521(14) Uani 1 1 d . . . . .
H3 H 0.481991 0.144577 0.626670 0.063 Uiso 1 1 calc R . . . .
C10 C 0.4793(3) 0.3281(2) 0.6009(9) 0.0470(14) Uani 1 1 d . . . . .
H10 H 0.442843 0.352619 0.596954 0.056 Uiso 1 1 calc R . . . .
C5 C 0.4588(4) 0.2099(2) 0.6166(11) 0.0510(14) Uani 1 1 d . . . . .
H5 H 0.399280 0.207386 0.617184 0.061 Uiso 1 1 calc R . . . .
C13 C 0.7038(5) 0.4373(2) 0.4834(14) 0.079(2) Uani 1 1 d . . . . .
H13 H 0.751643 0.444254 0.410380 0.095 Uiso 1 1 calc R . . . .
C16 C 0.5622(4) 0.4166(2) 0.6996(11) 0.0610(18) Uani 1 1 d . . . . .
H16 H 0.513845 0.410182 0.771863 0.073 Uiso 1 1 calc R . . . .
C14 C 0.6641(6) 0.4696(3) 0.5861(15) 0.084(3) Uani 1 1 d . . . . .
H14 H 0.684656 0.498747 0.581646 0.101 Uiso 1 1 calc R . . . .
C15 C 0.5944(6) 0.4597(2) 0.6959(14) 0.079(2) Uani 1 1 d . . . . .
H15 H 0.568528 0.481947 0.768088 0.095 Uiso 1 1 calc R . . . .
C1 C 0.6178(6) 0.0652(3) 0.4519(17) 0.091(2) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0293(8) 0.0586(9) 0.0712(10) 0.0022(8) -0.0023(8) 0.0044(6)
S1 0.0559(10) 0.0557(9) 0.0604(9) -0.0002(10) -0.0033(9) 0.0162(7)
O2 0.077(3) 0.076(3) 0.054(3) 0.006(3) 0.003(3) 0.026(3)
O1 0.055(3) 0.052(2) 0.053(3) 0.008(2) 0.000(2) 0.005(2)
O3 0.063(3) 0.087(3) 0.091(4) 0.003(3) -0.010(3) 0.032(3)
N1 0.033(3) 0.064(3) 0.053(3) 0.001(3) 0.001(3) 0.005(2)
C7 0.032(3) 0.056(3) 0.030(3) 0.001(3) 0.003(3) 0.000(2)
F1 0.085(3) 0.094(3) 0.169(5) -0.008(4) -0.029(4) -0.013(3)
C8 0.029(3) 0.056(3) 0.041(3) -0.001(3) 0.002(3) 0.002(3)
C6 0.028(3) 0.056(3) 0.038(3) 0.001(3) 0.006(3) 0.000(3)
C11 0.043(3) 0.053(3) 0.043(3) 0.007(3) -0.003(3) 0.005(3)
C9 0.038(3) 0.056(3) 0.032(3) 0.003(3) 0.002(3) 0.006(3)
C12 0.064(4) 0.058(4) 0.062(4) 0.003(4) 0.008(4) -0.005(3)
C4 0.026(3) 0.054(3) 0.039(3) 0.000(3) -0.003(3) 0.003(2)
F3 0.172(8) 0.111(5) 0.220(8) -0.095(6) 0.033(7) -0.014(5)
C2 0.041(3) 0.054(3) 0.042(3) 0.002(3) 0.002(3) 0.006(3)
F2 0.170(6) 0.094(4) 0.172(6) 0.052(5) -0.026(6) -0.031(4)
C3 0.045(3) 0.056(3) 0.056(4) 0.004(3) 0.008(4) -0.010(3)
C10 0.037(3) 0.056(3) 0.049(4) 0.006(3) 0.003(3) 0.011(3)
C5 0.033(3) 0.066(4) 0.054(3) 0.000(4) 0.004(3) -0.003(3)
C13 0.089(6) 0.066(4) 0.081(5) 0.009(5) 0.016(5) -0.018(4)
C16 0.050(4) 0.063(4) 0.069(4) -0.003(4) -0.002(4) 0.016(3)
C14 0.097(6) 0.058(4) 0.099(6) 0.010(5) -0.013(6) -0.015(5)
C15 0.078(5) 0.059(5) 0.101(6) -0.013(4) -0.017(5) 0.016(4)
C1 0.093(7) 0.065(5) 0.116(7) -0.007(6) -0.009(7) 0.009(4)

_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
Cl1 C4 1.734(5) . ?
S1 O2 1.409(5) . ?
S1 O1 1.567(5) . ?
S1 O3 1.406(5) . ?
S1 C1 1.815(9) . ?
O1 C2 1.427(6) . ?
N1 C6 1.372(7) . ?
N1 C10 1.297(7) . ?
C7 C8 1.398(8) . ?
C7 C6 1.437(8) . ?
C7 C4 1.418(7) . ?
F1 C1 1.307(9) . ?
C8 C9 1.377(8) . ?
C6 C5 1.395(8) . ?
C11 C9 1.475(8) . ?
C11 C12 1.378(9) . ?
C11 C16 1.396(9) . ?
C9 C10 1.426(8) . ?
C12 C13 1.396(10) . ?
C4 C2 1.364(7) . ?
F3 C1 1.285(12) . ?
C2 C3 1.401(8) . ?
F2 C1 1.323(13) . ?
C3 C5 1.354(9) . ?
C13 C14 1.359(12) . ?
C16 C15 1.386(10) . ?
C14 C15 1.366(12) . ?

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
O2 S1 O1 110.5(2) . . ?
O2 S1 C1 107.0(4) . . ?
O1 S1 C1 99.0(4) . . ?
O3 S1 O2 123.7(3) . . ?
O3 S1 O1 107.7(3) . . ?
O3 S1 C1 106.0(4) . . ?
C2 O1 S1 121.4(4) . . ?
C10 N1 C6 118.4(5) . . ?
C8 C7 C6 117.8(5) . . ?
C8 C7 C4 125.0(5) . . ?
C4 C7 C6 117.2(5) . . ?
C9 C8 C7 121.0(5) . . ?
N1 C6 C7 121.0(5) . . ?
N1 C6 C5 118.7(5) . . ?
C5 C6 C7 120.4(5) . . ?
C12 C11 C9 120.5(6) . . ?
C12 C11 C16 118.6(6) . . ?
C16 C11 C9 120.9(6) . . ?
C8 C9 C11 123.1(5) . . ?
C8 C9 C10 116.3(5) . . ?
C10 C9 C11 120.6(5) . . ?
C11 C12 C13 120.3(7) . . ?
C7 C4 Cl1 120.7(4) . . ?
C2 C4 Cl1 119.5(4) . . ?
C2 C4 C7 119.9(5) . . ?
C4 C2 O1 119.5(5) . . ?
C4 C2 C3 122.3(5) . . ?
C3 C2 O1 118.0(5) . . ?
C5 C3 C2 119.2(6) . . ?
N1 C10 C9 125.5(5) . . ?
C3 C5 C6 121.0(6) . . ?
C14 C13 C12 120.2(8) . . ?
C15 C16 C11 120.3(7) . . ?
C13 C14 C15 120.6(7) . . ?
C14 C15 C16 120.0(7) . . ?
F1 C1 S1 111.9(5) . . ?
F1 C1 F2 106.2(9) . . ?
F3 C1 S1 110.5(8) . . ?
F3 C1 F1 109.5(9) . . ?
F3 C1 F2 107.9(8) . . ?
F2 C1 S1 110.8(7) . . ?
