# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_wj230
_database_code_depnum_ccdc_archive 'CCDC 1898035'
loop_
_audit_author_name
_audit_author_address
'Poisson Thomas'
;INSA Rouen
France
;
_audit_update_record             
;
2019-02-19 deposited with the CCDC.	2019-03-25 downloaded from the CCDC.
;

_audit_creation_date             2018-05-18T14:04:01-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C19 H20 Cl1 F2 O3 P1 S1'
_chemical_formula_sum            'C19 H20 Cl F2 O3 P S'
_chemical_formula_weight         432.83
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.099(2)
_cell_length_b                   10.253(2)
_cell_length_c                   11.362(2)
_cell_angle_alpha                77.012(4)
_cell_angle_beta                 67.262(4)
_cell_angle_gamma                83.234(4)
_cell_volume                     1056.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2525
_cell_measurement_theta_min      1.98
_cell_measurement_theta_max      26.39
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0
_exptl_crystal_size_mid          0
_exptl_crystal_size_min          0
_exptl_crystal_density_diffrn    1.36
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             448
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.388
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'SMART APEX I Bruker'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0403
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_number            8217
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.98
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_full        26.39
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_reflns_number_total             4152
_reflns_number_gt                2525
_reflns_threshold_expression     >2σ(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       SMART
_computing_cell_refinement       SMART
_computing_data_reduction        SAINT
_computing_structure_solution    SHELXS-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2σ(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0975P)²+0.0881P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4152
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0656
_refine_ls_wR_factor_ref         0.207
_refine_ls_wR_factor_gt          0.1754
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_restrained_S_all      1.02
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.276
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3884(4) 0.3849(4) 0.2975(4) 0.0761(11) Uani 1 1 d . . .
H1 H 0.4247 0.4699 0.2586 0.091 Uiso 1 1 calc R . .
C2 C 0.4151(5) 0.2862(6) 0.2240(5) 0.0939(14) Uani 1 1 d . . .
H2 H 0.4704 0.3052 0.1355 0.113 Uiso 1 1 calc R . .
C3 C 0.3609(5) 0.1619(5) 0.2803(6) 0.0986(15) Uani 1 1 d . . .
H3 H 0.3779 0.0972 0.2299 0.118 Uiso 1 1 calc R . .
C4 C 0.2815(5) 0.1326(5) 0.4110(6) 0.0966(14) Uani 1 1 d . . .
H4 H 0.2447 0.0477 0.4491 0.116 Uiso 1 1 calc R . .
C5 C 0.2559(4) 0.2273(4) 0.4863(4) 0.0780(11) Uani 1 1 d . . .
H5 H 0.2041 0.2056 0.5754 0.094 Uiso 1 1 calc R . .
C6 C 0.3069(4) 0.3548(4) 0.4300(4) 0.0623(9) Uani 1 1 d . . .
C7 C 0.2757(4) 0.4594(4) 0.5105(3) 0.0636(9) Uani 1 1 d . . .
C8 C 0.2080(4) 0.5789(4) 0.4955(3) 0.0591(9) Uani 1 1 d . . .
C9 C 0.1845(4) 0.6812(3) 0.5777(4) 0.0638(9) Uani 1 1 d . . .
C10 C 0.2998(4) 0.7341(4) 0.5864(4) 0.0819(12) Uani 1 1 d . . .
H10 H 0.3932 0.7041 0.5438 0.098 Uiso 1 1 calc R . .
C11 C 0.2740(6) 0.8317(5) 0.6591(6) 0.1046(16) Uani 1 1 d . . .
H11 H 0.3511 0.8666 0.6658 0.126 Uiso 1 1 calc R . .
C12 C 0.1382(6) 0.8782(5) 0.7214(5) 0.1087(17) Uani 1 1 d . . .
H12 H 0.123 0.9454 0.7687 0.13 Uiso 1 1 calc R . .
C13 C 0.0248(6) 0.8255(5) 0.7137(5) 0.1044(16) Uani 1 1 d . . .
H13 H -0.0685 0.8551 0.7576 0.125 Uiso 1 1 calc R . .
C14 C 0.0482(4) 0.7282(4) 0.6407(4) 0.0817(12) Uani 1 1 d . . .
H14 H -0.0295 0.694 0.6342 0.098 Uiso 1 1 calc R . .
C15 C 0.2124(5) 0.7551(4) 0.2714(4) 0.0775(11) Uani 1 1 d . . .
Cl01 Cl 0.33044(13) 0.40991(11) 0.64225(10) 0.0898(4) Uani 1 1 d . . .
F1 F 0.3574(3) 0.7366(3) 0.2359(3) 0.1220(11) Uani 1 1 d . . .
F2 F 0.1807(4) 0.8650(3) 0.3269(3) 0.1295(11) Uani 1 1 d . . .
O2 O 0.2353(3) 0.6781(4) 0.0556(3) 0.1039(10) Uani 1 1 d . . .
O3 O 0.0109(3) 0.8148(3) 0.1616(3) 0.1029(10) Uani 1 1 d . . .
P3 P 0.16415(14) 0.79447(12) 0.12719(12) 0.0855(4) Uani 1 1 d . . .
S1 S 0.12229(9) 0.61052(9) 0.38225(9) 0.0615(3) Uani 1 1 d . . .
C16 C 0.1561(9) 0.5729(8) 0.0554(9) 0.198(4) Uani 1 1 d . . .
H16A H 0.1277 0.5154 0.1409 0.238 Uiso 1 1 calc R . .
H16B H 0.0688 0.6121 0.0436 0.238 Uiso 1 1 calc R . .
C17 C 0.2188(9) 0.4972(9) -0.0313(8) 0.205(4) Uani 1 1 d . . .
H17A H 0.2268 0.5472 -0.1159 0.307 Uiso 1 1 calc R . .
H17B H 0.1625 0.42 -0.0102 0.307 Uiso 1 1 calc R . .
H17C H 0.3129 0.4689 -0.0313 0.307 Uiso 1 1 calc R . .
C18 C 0.2439(8) 1.0204(6) -0.0362(7) 0.151(2) Uani 1 1 d . . .
H18A H 0.2296 0.9884 -0.1043 0.182 Uiso 1 1 calc R . .
H18B H 0.1533 1.0619 0.0114 0.182 Uiso 1 1 calc R . .
C19 C 0.3347(8) 1.1154(7) -0.0937(8) 0.185(4) Uani 1 1 d . . .
H19A H 0.2958 1.194 -0.0575 0.277 Uiso 1 1 calc R . .
H19B H 0.3525 1.1354 -0.1851 0.277 Uiso 1 1 calc R . .
H19C H 0.4232 1.0873 -0.081 0.277 Uiso 1 1 calc R . .
O4 O 0.2654(4) 0.9118(4) 0.0458(5) 0.1546(18) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C1 C6 1.389(5) . ?
C1 C2 1.392(5) . ?
C1 H1 0.93 . ?
C2 C3 1.363(7) . ?
C2 H2 0.93 . ?
C3 C4 1.369(7) . ?
C3 H3 0.93 . ?
C4 C5 1.373(6) . ?
C4 H4 0.93 . ?
C5 C6 1.383(5) . ?
C5 H5 0.93 . ?
C6 C7 1.491(5) . ?
C7 C8 1.341(5) . ?
C7 Cl01 1.743(4) . ?
C8 C9 1.496(4) . ?
C8 S1 1.766(4) . ?
C9 C14 1.369(5) . ?
C9 C10 1.386(5) . ?
C10 C11 1.376(5) . ?
C10 H10 0.93 . ?
C11 C12 1.363(6) . ?
C11 H11 0.93 . ?
C12 C13 1.363(7) . ?
C12 H12 0.93 . ?
C13 C14 1.380(5) . ?
C13 H13 0.93 . ?
C14 H14 0.93 . ?
C15 F2 1.360(4) . ?
C15 F1 1.362(5) . ?
C15 S1 1.790(4) . ?
C15 P3 1.833(4) . ?
O2 C16 1.417(7) . ?
O2 P3 1.544(3) . ?
O3 P3 1.444(3) . ?
P3 O4 1.551(4) . ?
C16 C17 1.312(8) . ?
C16 H16A 0.97 . ?
C16 H16B 0.97 . ?
C17 H17A 0.96 . ?
C17 H17B 0.96 . ?
C17 H17C 0.96 . ?
C18 C19 1.296(7) . ?
C18 O4 1.337(7) . ?
C18 H18A 0.97 . ?
C18 H18B 0.97 . ?
C19 H19A 0.96 . ?
C19 H19B 0.96 . ?
C19 H19C 0.96 . ?

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
C6 C1 C2 119.1(4) . . ?
C6 C1 H1 120.5 . . ?
C2 C1 H1 120.5 . . ?
C3 C2 C1 120.7(5) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C3 C4 119.9(4) . . ?
C2 C3 H3 120 . . ?
C4 C3 H3 120 . . ?
C3 C4 C5 120.6(5) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.5(4) . . ?
C5 C6 C7 120.4(3) . . ?
C1 C6 C7 120.0(3) . . ?
C8 C7 C6 128.0(3) . . ?
C8 C7 Cl01 119.0(3) . . ?
C6 C7 Cl01 112.9(3) . . ?
C7 C8 C9 125.2(3) . . ?
C7 C8 S1 117.3(3) . . ?
C9 C8 S1 117.1(3) . . ?
C14 C9 C10 119.1(3) . . ?
C14 C9 C8 120.0(3) . . ?
C10 C9 C8 120.8(3) . . ?
C11 C10 C9 119.1(4) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C12 C11 C10 121.6(4) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
C13 C12 C11 119.4(4) . . ?
C13 C12 H12 120.3 . . ?
C11 C12 H12 120.3 . . ?
C12 C13 C14 120.0(4) . . ?
C12 C13 H13 120 . . ?
C14 C13 H13 120 . . ?
C9 C14 C13 120.9(4) . . ?
C9 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
F2 C15 F1 104.4(3) . . ?
F2 C15 S1 112.2(3) . . ?
F1 C15 S1 110.7(3) . . ?
F2 C15 P3 108.1(3) . . ?
F1 C15 P3 110.3(3) . . ?
S1 C15 P3 111.0(2) . . ?
C16 O2 P3 122.7(4) . . ?
O3 P3 O2 116.4(2) . . ?
O3 P3 O4 119.9(2) . . ?
O2 P3 O4 103.0(2) . . ?
O3 P3 C15 111.7(2) . . ?
O2 P3 C15 103.64(19) . . ?
O4 P3 C15 99.7(2) . . ?
C8 S1 C15 101.77(18) . . ?
C17 C16 O2 117.9(7) . . ?
C17 C16 H16A 107.8 . . ?
O2 C16 H16A 107.8 . . ?
C17 C16 H16B 107.8 . . ?
O2 C16 H16B 107.8 . . ?
H16A C16 H16B 107.2 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 O4 123.1(7) . . ?
C19 C18 H18A 106.5 . . ?
O4 C18 H18A 106.5 . . ?
C19 C18 H18B 106.5 . . ?
O4 C18 H18B 106.5 . . ?
H18A C18 H18B 106.5 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 O4 P3 129.1(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
C6 C1 C2 C3 0.7(6) . . . . ?
C1 C2 C3 C4 -1.2(7) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 1.7(7) . . . . ?
C4 C5 C6 C1 -2.2(6) . . . . ?
C4 C5 C6 C7 178.2(4) . . . . ?
C2 C1 C6 C5 1.0(6) . . . . ?
C2 C1 C6 C7 -179.4(3) . . . . ?
C5 C6 C7 C8 -121.6(4) . . . . ?
C1 C6 C7 C8 58.8(5) . . . . ?
C5 C6 C7 Cl01 55.6(4) . . . . ?
C1 C6 C7 Cl01 -124.0(3) . . . . ?
C6 C7 C8 C9 -177.9(3) . . . . ?
Cl01 C7 C8 C9 5.1(5) . . . . ?
C6 C7 C8 S1 9.7(5) . . . . ?
Cl01 C7 C8 S1 -167.27(18) . . . . ?
C7 C8 C9 C14 -123.8(4) . . . . ?
S1 C8 C9 C14 48.6(4) . . . . ?
C7 C8 C9 C10 59.2(5) . . . . ?
S1 C8 C9 C10 -128.4(4) . . . . ?
C14 C9 C10 C11 0.5(7) . . . . ?
C8 C9 C10 C11 177.5(4) . . . . ?
C9 C10 C11 C12 -0.7(8) . . . . ?
C10 C11 C12 C13 1.2(9) . . . . ?
C11 C12 C13 C14 -1.6(8) . . . . ?
C10 C9 C14 C13 -1.0(7) . . . . ?
C8 C9 C14 C13 -178.0(4) . . . . ?
C12 C13 C14 C9 1.5(8) . . . . ?
C16 O2 P3 O3 -17.9(6) . . . . ?
C16 O2 P3 O4 -151.3(6) . . . . ?
C16 O2 P3 C15 105.1(6) . . . . ?
F2 C15 P3 O3 -66.4(3) . . . . ?
F1 C15 P3 O3 -179.9(3) . . . . ?
S1 C15 P3 O3 57.0(3) . . . . ?
F2 C15 P3 O2 167.5(3) . . . . ?
F1 C15 P3 O2 54.0(3) . . . . ?
S1 C15 P3 O2 -69.1(3) . . . . ?
F2 C15 P3 O4 61.4(3) . . . . ?
F1 C15 P3 O4 -52.1(3) . . . . ?
S1 C15 P3 O4 -175.2(3) . . . . ?
C7 C8 S1 C15 -120.7(3) . . . . ?
C9 C8 S1 C15 66.3(3) . . . . ?
F2 C15 S1 C8 -68.1(3) . . . . ?
F1 C15 S1 C8 48.0(3) . . . . ?
P3 C15 S1 C8 170.8(2) . . . . ?
P3 O2 C16 C17 164.3(7) . . . . ?
C19 C18 O4 P3 176.3(6) . . . . ?
O3 P3 O4 C18 -24.4(8) . . . . ?
O2 P3 O4 C18 106.9(7) . . . . ?
C15 P3 O4 C18 -146.6(6) . . . . ?
