# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2190657'
loop_
_audit_author_name
_audit_author_address
'Maria del Carmen Munoz Roca'
;Departament de Fisica Aplicada, Universitat Politecnica de Valencia
Spain
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2022-11-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H11 F2 N O3 S'
_chemical_formula_weight         299.29

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'
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   8.1283(4)
_cell_length_b                   10.6899(6)
_cell_length_c                   15.0823(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1310.51(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    7962
_cell_measurement_theta_min      2.8467
_cell_measurement_theta_max      29.7157

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.517
_exptl_crystal_F_000             616
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.277
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.830
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'Empirical absorption correction'

_exptl_special_details           
;
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker S8 x-ray diffraction'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36330
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0709
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.335
_diffrn_reflns_theta_max         30.535
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4006
_reflns_number_gt                2908
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'APEX3, Bruker'
_computing_cell_refinement       'APEX3, Bruker'
_computing_data_reduction        'APEX3, Bruker'
_computing_structure_solution    SHELXS-2014
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0504P)²+0.3074P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1035 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4006
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0739
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1096
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.03632(10) 0.40341(9) 0.67949(6) 0.0503(2) Uani 1 1 d . . . . .
F1 F 0.3723(3) 0.73589(16) 0.66394(14) 0.0528(5) Uani 1 1 d . . . . .
F2 F 0.4450(2) 0.68334(16) 0.53058(11) 0.0480(4) Uani 1 1 d . . . . .
O1 O 0.5811(3) 0.5404(2) 0.73308(13) 0.0408(5) Uani 1 1 d . . . . .
O2 O 0.2723(3) 0.4817(2) 0.54117(13) 0.0488(6) Uani 1 1 d . . . . .
O3 O 0.5436(3) 0.33635(19) 0.65163(13) 0.0464(5) Uani 1 1 d . . . . .
N1 N 0.6368(3) 0.3805(2) 0.58699(14) 0.0316(5) Uani 1 1 d . . . . .
C1 C 0.5975(3) 0.5944(3) 0.64887(17) 0.0325(5) Uani 1 1 d . . . . .
C2 C 0.4261(4) 0.6370(2) 0.61445(18) 0.0352(6) Uani 1 1 d . . . . .
C3 C 0.2904(3) 0.5367(3) 0.61057(17) 0.0346(6) Uani 1 1 d . . . . .
C4 C 0.7068(5) 0.7095(3) 0.6612(3) 0.0552(9) Uani 1 1 d . . . . .
H4A H 0.6672 0.7582 0.7110 0.083 Uiso 1 1 calc R U . . .
H4B H 0.7035 0.7602 0.6079 0.083 Uiso 1 1 calc R U . . .
H4C H 0.8191 0.6830 0.6724 0.083 Uiso 1 1 calc R U . . .
C5 C 0.6699(3) 0.5046(2) 0.57980(16) 0.0285(5) Uani 1 1 d . . . . .
C6 C 0.7680(4) 0.5438(3) 0.51033(19) 0.0410(7) Uani 1 1 d . . . . .
H6 H 0.7937 0.6292 0.5048 0.049 Uiso 1 1 calc R U . . .
C7 C 0.8288(4) 0.4604(4) 0.4491(2) 0.0497(8) Uani 1 1 d . . . . .
H7 H 0.8943 0.4883 0.4017 0.060 Uiso 1 1 calc R U . . .
C8 C 0.7922(4) 0.3357(4) 0.4583(2) 0.0491(8) Uani 1 1 d . . . . .
H8 H 0.8322 0.2771 0.4171 0.059 Uiso 1 1 calc R U . . .
C9 C 0.6976(4) 0.2979(3) 0.5274(2) 0.0414(7) Uani 1 1 d . . . . .
H9 H 0.6737 0.2124 0.5341 0.050 Uiso 1 1 calc R U . . .
C10 C 0.1901(3) 0.5132(3) 0.68831(18) 0.0362(6) Uani 1 1 d . . . . .
C11 C 0.1961(4) 0.5636(3) 0.77450(19) 0.0427(7) Uani 1 1 d . . . . .
H11 H 0.2719 0.6243 0.7936 0.051 Uiso 1 1 calc R U . . .
C12 C 0.0739(4) 0.5110(4) 0.8277(2) 0.0578(9) Uani 1 1 d . . . . .
H12 H 0.0585 0.5331 0.8875 0.069 Uiso 1 1 calc R U . . .
C13 C -0.0202(4) 0.4253(4) 0.7858(2) 0.0587(10) Uani 1 1 d . . . . .
H13 H -0.1077 0.3825 0.8130 0.070 Uiso 1 1 calc R U . . .
H1O H 0.560(4) 0.477(3) 0.725(2) 0.031(9) Uiso 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
S1 C13 1.685(4) . ?
S1 C10 1.720(3) . ?
F1 C2 1.366(3) . ?
F2 C2 1.367(3) . ?
O1 C1 1.402(3) . ?
O1 H1O 0.71(3) . ?
O2 C3 1.210(3) . ?
O3 N1 1.322(3) . ?
N1 C9 1.353(4) . ?
N1 C5 1.357(3) . ?
C1 C4 1.528(4) . ?
C1 C5 1.534(3) . ?
C1 C2 1.555(4) . ?
C2 C3 1.540(4) . ?
C3 C10 1.450(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 H4C 0.9700 . ?
C5 C6 1.382(4) . ?
C6 C7 1.376(4) . ?
C6 H6 0.9400 . ?
C7 C8 1.373(5) . ?
C7 H7 0.9400 . ?
C8 C9 1.357(5) . ?
C8 H8 0.9400 . ?
C9 H9 0.9400 . ?
C10 C11 1.408(4) . ?
C11 C12 1.396(5) . ?
C11 H11 0.9400 . ?
C12 C13 1.350(6) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?

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
C13 S1 C10 91.70(17) . . ?
C1 O1 H1O 105(3) . . ?
O3 N1 C9 117.7(2) . . ?
O3 N1 C5 121.5(2) . . ?
C9 N1 C5 120.8(2) . . ?
O1 C1 C4 106.1(2) . . ?
O1 C1 C5 113.2(2) . . ?
C4 C1 C5 111.3(2) . . ?
O1 C1 C2 109.8(2) . . ?
C4 C1 C2 109.0(3) . . ?
C5 C1 C2 107.5(2) . . ?
F1 C2 F2 105.2(2) . . ?
F1 C2 C3 109.3(2) . . ?
F2 C2 C3 107.3(2) . . ?
F1 C2 C1 109.3(2) . . ?
F2 C2 C1 108.3(2) . . ?
C3 C2 C1 116.8(2) . . ?
O2 C3 C10 123.2(3) . . ?
O2 C3 C2 117.3(3) . . ?
C10 C3 C2 119.5(2) . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 118.2(2) . . ?
N1 C5 C1 118.8(2) . . ?
C6 C5 C1 123.1(3) . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 119.0(3) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C7 119.3(3) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
N1 C9 C8 121.5(3) . . ?
N1 C9 H9 119.2 . . ?
C8 C9 H9 119.2 . . ?
C11 C10 C3 131.4(3) . . ?
C11 C10 S1 110.9(2) . . ?
C3 C10 S1 117.7(2) . . ?
C12 C11 C10 110.6(3) . . ?
C12 C11 H11 124.7 . . ?
C10 C11 H11 124.7 . . ?
C13 C12 C11 114.0(3) . . ?
C13 C12 H12 123.0 . . ?
C11 C12 H12 123.0 . . ?
C12 C13 S1 112.7(3) . . ?
C12 C13 H13 123.7 . . ?
S1 C13 H13 123.7 . . ?

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
O1 C1 C2 F1 69.0(3) . . . . ?
C4 C1 C2 F1 -46.8(3) . . . . ?
C5 C1 C2 F1 -167.5(2) . . . . ?
O1 C1 C2 F2 -177.0(2) . . . . ?
C4 C1 C2 F2 67.3(3) . . . . ?
C5 C1 C2 F2 -53.5(3) . . . . ?
O1 C1 C2 C3 -55.7(3) . . . . ?
C4 C1 C2 C3 -171.5(2) . . . . ?
C5 C1 C2 C3 67.8(3) . . . . ?
F1 C2 C3 O2 141.7(3) . . . . ?
F2 C2 C3 O2 28.2(3) . . . . ?
C1 C2 C3 O2 -93.5(3) . . . . ?
F1 C2 C3 C10 -37.6(3) . . . . ?
F2 C2 C3 C10 -151.1(2) . . . . ?
C1 C2 C3 C10 87.1(3) . . . . ?
O3 N1 C5 C6 -179.8(2) . . . . ?
C9 N1 C5 C6 -0.3(4) . . . . ?
O3 N1 C5 C1 0.3(4) . . . . ?
C9 N1 C5 C1 179.8(2) . . . . ?
O1 C1 C5 N1 32.0(3) . . . . ?
C4 C1 C5 N1 151.4(3) . . . . ?
C2 C1 C5 N1 -89.3(3) . . . . ?
O1 C1 C5 C6 -147.9(3) . . . . ?
C4 C1 C5 C6 -28.5(4) . . . . ?
C2 C1 C5 C6 90.8(3) . . . . ?
N1 C5 C6 C7 1.0(4) . . . . ?
C1 C5 C6 C7 -179.1(3) . . . . ?
C5 C6 C7 C8 -0.7(5) . . . . ?
C6 C7 C8 C9 -0.2(5) . . . . ?
O3 N1 C9 C8 179.0(3) . . . . ?
C5 N1 C9 C8 -0.6(4) . . . . ?
C7 C8 C9 N1 0.8(5) . . . . ?
O2 C3 C10 C11 177.5(3) . . . . ?
C2 C3 C10 C11 -3.3(5) . . . . ?
O2 C3 C10 S1 -1.1(4) . . . . ?
C2 C3 C10 S1 178.2(2) . . . . ?
C13 S1 C10 C11 0.9(2) . . . . ?
C13 S1 C10 C3 179.7(2) . . . . ?
C3 C10 C11 C12 -179.4(3) . . . . ?
S1 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
C11 C12 C13 S1 0.5(4) . . . . ?
C10 S1 C13 C12 -0.8(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 F2 0.94 2.41 3.310(4) 160.0 2_566

_refine_diff_density_max         0.194
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.045

_shelxl_version_number           2014-1

