# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mo_vb_a_762_vesely
_database_code_depnum_ccdc_archive 'CCDC 2162666'
loop_
_audit_author_name
_audit_author_address
'Ivana Cisarova'
;Charles Univerzity
Czech Republic
;
_audit_update_record             
;
2022-03-28 deposited with the CCDC.	2022-08-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 Cl2 F N O4 S'
_chemical_formula_sum            'C23 H16 Cl2 F N O4 S'
_chemical_formula_weight         492.33
_chemical_compound_source        'synthesized by the authors'

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'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.4760(5)
_cell_length_b                   14.1768(7)
_cell_length_c                   14.4461(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2145.48(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9686
_cell_measurement_theta_min      3.7156
_cell_measurement_theta_max      30.0008

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             1008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.396
_exptl_crystal_size_mid          0.254
_exptl_crystal_size_min          0.230
_exptl_absorpt_coefficient_mu    0.441
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
"Comparison of silver and molybdenum microfocus X-ray sources for
single-crystal structure determination"
J. Appl. Cryst. 48, 3-10.
doi:10.1107/S1600576714022985
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'I\mS  micro-focus sealed tube'
_diffrn_radiation_monochromator  'Quazar Mo multilayer optic'

_diffrn_measurement_device_type  'Bruker D8 VENTURE Kappa Duo PHOTONIII CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            121548
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.013
_diffrn_reflns_theta_max         30.009
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             6247
_reflns_number_gt                6217
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.784
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.996

_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       'Bruker Instrument Service vV6.2.15'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_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)+(0.0309P)²+0.4301P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2724 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.004(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         6247
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0203
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_ref         0.0567
_refine_ls_wR_factor_gt          0.0566
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_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
Cl1 Cl 0.96987(4) 0.81874(3) -0.08227(3) 0.03066(9) Uani 1 1 d . . . . .
Cl2 Cl 1.23691(4) 0.77487(3) -0.17331(3) 0.02969(9) Uani 1 1 d . . . . .
S1 S 0.94357(3) 0.38427(2) 0.22249(2) 0.01355(6) Uani 1 1 d . . . . .
F1 F 0.91120(8) 0.55744(6) 0.16907(6) 0.01570(15) Uani 1 1 d . . . . .
O1 O 1.27798(10) 0.39176(8) -0.05741(8) 0.0249(2) Uani 1 1 d . . . . .
O2 O 1.21084(10) 0.45043(9) 0.17589(8) 0.0263(2) Uani 1 1 d . . . . .
O3 O 0.98869(11) 0.29927(7) 0.17894(8) 0.0208(2) Uani 1 1 d . . . . .
O4 O 0.98811(10) 0.41030(8) 0.31325(7) 0.0203(2) Uani 1 1 d . . . . .
N1 N 1.08058(11) 0.39660(8) 0.01378(8) 0.0152(2) Uani 1 1 d . . . . .
H1 H 1.085840 0.343290 0.038940 0.023 Uiso 1 1 d R U . . .
C1 C 1.18221(13) 0.43390(10) -0.03359(10) 0.0172(2) Uani 1 1 d . . . . .
C2 C 0.98274(12) 0.46436(9) 0.04005(8) 0.0123(2) Uani 1 1 d . . . . .
C3 C 1.03067(12) 0.55296(9) -0.00937(9) 0.0138(2) Uani 1 1 d . . . . .
C4 C 0.97498(13) 0.64142(9) -0.01762(9) 0.0168(2) Uani 1 1 d . . . . .
H4 H 0.894989 0.654996 0.010351 0.020 Uiso 1 1 calc R U . . .
C5 C 1.04052(14) 0.70967(9) -0.06839(10) 0.0189(3) Uani 1 1 d . . . . .
C6 C 1.15918(15) 0.69007(10) -0.10890(10) 0.0198(3) Uani 1 1 d . . . . .
C7 C 1.21479(14) 0.60187(10) -0.09996(9) 0.0189(3) Uani 1 1 d . . . . .
H7 H 1.295551 0.588290 -0.126740 0.023 Uiso 1 1 calc R U . . .
C8 C 1.14805(13) 0.53423(10) -0.05045(9) 0.0157(2) Uani 1 1 d . . . . .
C9 C 0.99205(12) 0.48363(9) 0.14681(9) 0.0128(2) Uani 1 1 d . . . . .
C10 C 1.12953(13) 0.51041(11) 0.17757(10) 0.0180(2) Uani 1 1 d . . . . .
C11 C 1.15062(16) 0.60939(12) 0.20973(12) 0.0275(3) Uani 1 1 d . . . . .
H11A H 1.118531 0.653452 0.162928 0.041 Uiso 1 1 calc R U . . .
H11B H 1.242115 0.620085 0.219212 0.041 Uiso 1 1 calc R U . . .
H11C H 1.105058 0.619527 0.268133 0.041 Uiso 1 1 calc R U . . .
C12 C 0.84952(12) 0.43451(9) 0.00683(8) 0.0129(2) Uani 1 1 d . . . . .
C13 C 0.83545(13) 0.35090(10) -0.04262(9) 0.0171(2) Uani 1 1 d . . . . .
H13 H 0.907519 0.311382 -0.052076 0.021 Uiso 1 1 calc R U . . .
C14 C 0.71707(14) 0.32413(10) -0.07858(10) 0.0198(3) Uani 1 1 d . . . . .
H14 H 0.709770 0.267646 -0.113566 0.024 Uiso 1 1 calc R U . . .
C15 C 0.61045(13) 0.37959(11) -0.06341(10) 0.0198(3) Uani 1 1 d . . . . .
H15 H 0.529583 0.360936 -0.086880 0.024 Uiso 1 1 calc R U . . .
C16 C 0.62293(13) 0.46330(10) -0.01324(10) 0.0188(3) Uani 1 1 d . . . . .
H16 H 0.550065 0.501655 -0.002481 0.023 Uiso 1 1 calc R U . . .
C17 C 0.74127(13) 0.49098(9) 0.02112(9) 0.0156(2) Uani 1 1 d . . . . .
H17 H 0.748810 0.548470 0.054470 0.019 Uiso 1 1 calc R U . . .
C18 C 0.77623(12) 0.38467(10) 0.22219(9) 0.0151(2) Uani 1 1 d . . . . .
C19 C 0.71328(14) 0.31211(11) 0.17619(10) 0.0207(3) Uani 1 1 d . . . . .
H19 H 0.759434 0.262714 0.146963 0.025 Uiso 1 1 calc R U . . .
C20 C 0.58068(16) 0.31423(14) 0.17438(12) 0.0304(4) Uani 1 1 d . . . . .
H20 H 0.535085 0.264102 0.145898 0.036 Uiso 1 1 calc R U . . .
C21 C 0.51409(15) 0.38885(15) 0.21378(11) 0.0321(4) Uani 1 1 d . . . . .
H21 H 0.423688 0.391047 0.209112 0.038 Uiso 1 1 calc R U . . .
C22 C 0.57871(15) 0.46020(14) 0.25989(11) 0.0273(3) Uani 1 1 d . . . . .
H22 H 0.532268 0.510640 0.287085 0.033 Uiso 1 1 calc R U . . .
C23 C 0.71111(14) 0.45825(11) 0.26649(10) 0.0192(3) Uani 1 1 d . . . . .
H23 H 0.756035 0.505377 0.300014 0.023 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
Cl1 C5 1.7260(15) . ?
Cl2 C6 1.7245(14) . ?
S1 O3 1.4393(11) . ?
S1 O4 1.4398(10) . ?
S1 C18 1.7530(13) . ?
S1 C9 1.8540(13) . ?
F1 C9 1.3841(14) . ?
O1 C1 1.2173(17) . ?
O2 C10 1.2038(19) . ?
N1 C1 1.3717(17) . ?
N1 C2 1.4550(16) . ?
N1 H1 0.8405 . ?
C1 C8 1.4868(19) . ?
C2 C3 1.5296(17) . ?
C2 C12 1.5353(18) . ?
C2 C9 1.5693(18) . ?
C3 C4 1.3882(18) . ?
C3 C8 1.3909(17) . ?
C4 C5 1.3949(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.402(2) . ?
C6 C7 1.386(2) . ?
C7 C8 1.3855(19) . ?
C7 H7 0.9500 . ?
C9 C10 1.5544(18) . ?
C10 C11 1.495(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.3918(18) . ?
C12 C17 1.4034(18) . ?
C13 C14 1.3970(19) . ?
C13 H13 0.9500 . ?
C14 C15 1.383(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.397(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.3919(18) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.3909(19) . ?
C18 C23 1.4011(19) . ?
C19 C20 1.390(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.389(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.390(2) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

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 O4 120.41(7) . . ?
O3 S1 C18 109.27(7) . . ?
O4 S1 C18 108.99(6) . . ?
O3 S1 C9 106.76(6) . . ?
O4 S1 C9 104.68(6) . . ?
C18 S1 C9 105.67(6) . . ?
C1 N1 C2 114.98(11) . . ?
C1 N1 H1 120.8 . . ?
C2 N1 H1 121.8 . . ?
O1 C1 N1 126.27(14) . . ?
O1 C1 C8 128.43(13) . . ?
N1 C1 C8 105.29(11) . . ?
N1 C2 C3 100.91(10) . . ?
N1 C2 C12 112.14(10) . . ?
C3 C2 C12 112.26(10) . . ?
N1 C2 C9 109.12(10) . . ?
C3 C2 C9 107.17(10) . . ?
C12 C2 C9 114.31(10) . . ?
C4 C3 C8 120.49(12) . . ?
C4 C3 C2 130.08(12) . . ?
C8 C3 C2 109.43(11) . . ?
C3 C4 C5 117.70(13) . . ?
C3 C4 H4 121.1 . . ?
C5 C4 H4 121.1 . . ?
C4 C5 C6 121.23(13) . . ?
C4 C5 Cl1 118.13(11) . . ?
C6 C5 Cl1 120.62(11) . . ?
C7 C6 C5 120.85(12) . . ?
C7 C6 Cl2 118.74(11) . . ?
C5 C6 Cl2 120.38(11) . . ?
C6 C7 C8 117.42(13) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
C7 C8 C3 122.29(13) . . ?
C7 C8 C1 128.69(13) . . ?
C3 C8 C1 109.00(11) . . ?
F1 C9 C10 108.42(10) . . ?
F1 C9 C2 108.78(10) . . ?
C10 C9 C2 112.40(10) . . ?
F1 C9 S1 105.65(8) . . ?
C10 C9 S1 105.71(9) . . ?
C2 C9 S1 115.48(9) . . ?
O2 C10 C11 124.39(13) . . ?
O2 C10 C9 118.51(13) . . ?
C11 C10 C9 117.08(12) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C17 118.41(12) . . ?
C13 C12 C2 119.43(11) . . ?
C17 C12 C2 122.10(11) . . ?
C12 C13 C14 121.08(13) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 120.23(13) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.31(12) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.53(13) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C12 120.42(12) . . ?
C16 C17 H17 119.8 . . ?
C12 C17 H17 119.8 . . ?
C19 C18 C23 122.54(13) . . ?
C19 C18 S1 118.22(11) . . ?
C23 C18 S1 119.23(10) . . ?
C20 C19 C18 117.84(16) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
C21 C20 C19 120.71(16) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C22 C21 C20 120.46(14) . . ?
C22 C21 H21 119.8 . . ?
C20 C21 H21 119.8 . . ?
C21 C22 C23 120.34(16) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C22 C23 C18 117.98(15) . . ?
C22 C23 H23 121.0 . . ?
C18 C23 H23 121.0 . . ?

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
_geom_hbond_publ_flag
N1 H1 O3 0.84 2.35 2.9195(16) 125.7 . yes

_refine_diff_density_max         0.320
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.040



