# 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. 
# 
#######################################################################

data_y
_database_code_depnum_ccdc_archive 'CCDC 1846319'
_audit_update_record             
;
2018-05-30 deposited with the CCDC.
2018-11-16 downloaded from the CCDC.
;
_audit_creation_date             2018-04-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C18 H12 Cl3 O P S3'
_chemical_formula_sum            'C18 H12 Cl3 O P S3'
_chemical_formula_weight         477.78
_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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y, -z+1/2'
3 'x+1/2, y+1/2, z'
4 '-x+1/2, y+1/2, -z+1/2'
5 '-x, -y, -z'
6 'x, -y, z-1/2'
7 '-x+1/2, -y+1/2, -z'
8 'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.268(2)
_cell_length_b                   8.6753(17)
_cell_length_c                   37.965(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.878(3)
_cell_angle_gamma                90.00
_cell_volume                     4035.5(13)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6288
_cell_measurement_temperature    273.15
_cell_measurement_theta_max      27.69
_cell_measurement_theta_min      2.88
_exptl_absorpt_coefficient_mu    0.850
_exptl_absorpt_correction_T_max  0.8484
_exptl_absorpt_correction_T_min  0.8484
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1936
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_special_details           
'The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of ω scans each set at different φ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.948 cm.'
_diffrn_reflns_av_R_equivalents  0.1323
_diffrn_reflns_av_unetI/netI     0.0805
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       45
_diffrn_reflns_limit_l_min       -45
_diffrn_reflns_number            13996
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.07
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.35
_diffrn_source_voltage           45.0
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                3165
_reflns_number_total             3545
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v6.28A (Bruker, 2002)'
_computing_data_collection       'SMART v5.625 (Bruker, 2001)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3545
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0596
_refine_ls_R_factor_gt           0.0534
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0487P)²+4.0964P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1351
_refine_ls_wR_factor_ref         0.1390
_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 > 2sigma(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. 
;
_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), C9(H9), C11(H11), C2(H2), C3(H3), C18(H18), C6(H6), C5(H5),
 C15(H15), C14(H14), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
S2 S 0.32879(6) 0.52679(9) 0.37747(2) 0.0370(2) Uani 1 d . . .
Cl2 Cl 0.61073(7) 0.97659(10) 0.29100(2) 0.0509(3) Uani 1 d . . .
P1 P 0.43095(7) 0.38016(10) 0.40680(2) 0.0393(2) Uani 1 d . . .
S1 S 0.49716(7) 0.21168(10) 0.37505(3) 0.0490(3) Uani 1 d . . .
Cl3 Cl 0.11854(10) 0.70289(11) 0.54237(3) 0.0628(3) Uani 1 d . . .
S3 S 0.31874(10) 0.25474(10) 0.43407(3) 0.0567(3) Uani 1 d . . .
Cl1 Cl 0.12412(9) -0.05530(13) 0.27431(3) 0.0652(3) Uani 1 d . . .
O1 O 0.5204(2) 0.4557(3) 0.42709(7) 0.0596(8) Uani 1 d . . .
C7 C 0.4204(2) 0.6410(3) 0.35338(8) 0.0301(6) Uani 1 d . . .
C10 C 0.5389(2) 0.8422(3) 0.31509(8) 0.0335(7) Uani 1 d . . .
C8 C 0.3936(3) 0.6636(3) 0.31803(8) 0.0351(7) Uani 1 d . . .
H8 H 0.3361 0.6089 0.3071 0.042 Uiso 1 calc . . R
C12 C 0.5094(3) 0.7172(3) 0.36937(8) 0.0361(7) Uani 1 d . . .
H12 H 0.5283 0.7012 0.3931 0.043 Uiso 1 calc . . R
C9 C 0.4517(3) 0.7666(4) 0.29887(8) 0.0374(7) Uani 1 d . . .
H9 H 0.4322 0.7849 0.2752 0.045 Uiso 1 calc . . R
C11 C 0.5693(3) 0.8165(4) 0.34969(9) 0.0385(7) Uani 1 d . . .
H11 H 0.6302 0.8660 0.3599 0.046 Uiso 1 calc . . R
C1 C 0.3839(3) 0.1446(4) 0.34799(9) 0.0394(8) Uani 1 d . . .
C16 C 0.1778(3) 0.5880(4) 0.51091(9) 0.0427(8) Uani 1 d . . .
C13 C 0.2676(3) 0.3970(4) 0.46311(8) 0.0420(8) Uani 1 d . . .
C2 C 0.3167(3) 0.0285(4) 0.35941(9) 0.0411(8) Uani 1 d . . .
H2 H 0.3268 -0.0100 0.3822 0.049 Uiso 1 calc . . R
C3 C 0.2351(3) -0.0300(4) 0.33716(10) 0.0448(9) Uani 1 d . . .
H3 H 0.1887 -0.1061 0.3450 0.054 Uiso 1 calc . . R
C4 C 0.2228(3) 0.0251(4) 0.30327(10) 0.0433(8) Uani 1 d . . .
C18 C 0.3249(3) 0.4311(4) 0.49433(9) 0.0448(8) Uani 1 d . . .
H18 H 0.3938 0.3889 0.4990 0.054 Uiso 1 calc . . R
C6 C 0.3686(3) 0.2018(4) 0.31383(9) 0.0447(8) Uani 1 d . . .
H6 H 0.4128 0.2810 0.3062 0.054 Uiso 1 calc . . R
C5 C 0.2887(3) 0.1419(4) 0.29138(10) 0.0463(9) Uani 1 d . . .
H5 H 0.2787 0.1791 0.2685 0.056 Uiso 1 calc . . R
C15 C 0.1212(3) 0.5579(4) 0.47955(9) 0.0467(8) Uani 1 d . . .
H15 H 0.0530 0.6020 0.4746 0.056 Uiso 1 calc . . R
C14 C 0.1665(3) 0.4619(4) 0.45558(9) 0.0467(9) Uani 1 d . . .
H14 H 0.1290 0.4406 0.4342 0.056 Uiso 1 calc . . R
C17 C 0.2802(3) 0.5274(4) 0.51852(9) 0.0455(9) Uani 1 d . . .
H17 H 0.3183 0.5513 0.5396 0.055 Uiso 1 calc . . R

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
S2 0.0274(4) 0.0400(4) 0.0433(5) 0.0054(3) 0.0004(3) -0.0089(3)
Cl2 0.0439(6) 0.0532(5) 0.0567(6) 0.0136(4) 0.0116(4) -0.0128(4)
P1 0.0393(5) 0.0388(5) 0.0392(5) 0.0073(3) -0.0030(4) -0.0082(4)
S1 0.0337(5) 0.0517(5) 0.0617(6) 0.0006(4) 0.0040(4) 0.0009(4)
Cl3 0.0782(8) 0.0573(6) 0.0552(6) -0.0103(4) 0.0243(5) -0.0207(5)
S3 0.0809(8) 0.0378(5) 0.0536(6) 0.0045(4) 0.0256(5) -0.0135(5)
Cl1 0.0511(6) 0.0737(7) 0.0700(7) -0.0229(5) -0.0035(5) 0.0010(5)
O1 0.0609(19) 0.0578(16) 0.0573(17) 0.0085(12) -0.0255(14) -0.0124(13)
C7 0.0259(16) 0.0269(14) 0.0375(17) -0.0013(12) 0.0015(12) -0.0019(11)
C10 0.0274(16) 0.0338(15) 0.0402(18) 0.0033(13) 0.0095(13) -0.0019(12)
C8 0.0294(17) 0.0382(17) 0.0372(17) -0.0072(13) -0.0029(13) -0.0058(13)
C12 0.0360(18) 0.0390(17) 0.0326(17) 0.0001(13) -0.0039(13) -0.0070(13)
C9 0.0366(19) 0.0443(17) 0.0315(17) 0.0005(13) 0.0034(13) -0.0037(14)
C11 0.0293(18) 0.0380(16) 0.048(2) -0.0003(14) -0.0009(14) -0.0090(13)
C1 0.0353(18) 0.0360(17) 0.0475(19) -0.0030(14) 0.0074(14) 0.0044(14)
C16 0.054(2) 0.0395(17) 0.0353(18) 0.0051(14) 0.0070(15) -0.0184(16)
C13 0.055(2) 0.0376(17) 0.0341(18) 0.0057(13) 0.0082(15) -0.0163(16)
C2 0.042(2) 0.0376(17) 0.044(2) 0.0043(14) 0.0079(15) 0.0046(15)
C3 0.041(2) 0.0343(17) 0.060(2) -0.0024(15) 0.0154(17) -0.0005(14)
C4 0.0367(19) 0.0397(17) 0.053(2) -0.0115(15) 0.0037(16) 0.0074(14)
C18 0.044(2) 0.0478(19) 0.042(2) 0.0174(16) -0.0036(15) -0.0073(16)
C6 0.046(2) 0.0377(17) 0.051(2) 0.0049(15) 0.0128(17) -0.0007(15)
C5 0.053(2) 0.0430(19) 0.044(2) 0.0018(15) 0.0082(17) 0.0094(16)
C15 0.039(2) 0.057(2) 0.044(2) 0.0038(16) 0.0031(15) -0.0115(16)
C14 0.046(2) 0.059(2) 0.0350(19) 0.0022(15) -0.0048(15) -0.0187(17)
C17 0.053(2) 0.049(2) 0.0335(18) 0.0087(15) -0.0048(16) -0.0200(17)

_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
S2 P1 2.0711(12) . ?
S2 C7 1.785(3) . ?
Cl2 C10 1.747(3) . ?
P1 S1 2.0850(13) . ?
P1 S3 2.0721(12) . ?
P1 O1 1.464(3) . ?
S1 C1 1.783(4) . ?
Cl3 C16 1.742(4) . ?
S3 C13 1.789(4) . ?
Cl1 C4 1.740(4) . ?
C7 C8 1.380(4) . ?
C7 C12 1.389(4) . ?
C10 C9 1.375(5) . ?
C10 C11 1.366(5) . ?
C8 C9 1.374(4) . ?
C12 C11 1.377(4) . ?
C1 C2 1.386(5) . ?
C1 C6 1.392(5) . ?
C16 C15 1.373(5) . ?
C16 C17 1.379(5) . ?
C13 C18 1.380(5) . ?
C13 C14 1.380(5) . ?
C2 C3 1.374(5) . ?
C3 C4 1.374(5) . ?
C4 C5 1.386(5) . ?
C18 C17 1.376(5) . ?
C6 C5 1.369(5) . ?
C15 C14 1.371(5) . ?

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
C7 S2 P1 103.69(11) . . ?
S2 P1 S1 111.25(5) . . ?
S2 P1 S3 101.06(6) . . ?
S3 P1 S1 102.04(5) . . ?
O1 P1 S2 115.18(11) . . ?
O1 P1 S1 108.34(13) . . ?
O1 P1 S3 118.14(12) . . ?
C1 S1 P1 104.30(11) . . ?
C13 S3 P1 102.00(11) . . ?
C8 C7 S2 116.8(2) . . ?
C8 C7 C12 120.1(3) . . ?
C12 C7 S2 122.8(2) . . ?
C9 C10 Cl2 119.1(2) . . ?
C11 C10 Cl2 119.5(2) . . ?
C11 C10 C9 121.5(3) . . ?
C9 C8 C7 120.2(3) . . ?
C11 C12 C7 119.3(3) . . ?
C8 C9 C10 119.1(3) . . ?
C10 C11 C12 119.8(3) . . ?
C2 C1 S1 121.1(3) . . ?
C2 C1 C6 119.7(3) . . ?
C6 C1 S1 119.0(3) . . ?
C15 C16 Cl3 119.6(3) . . ?
C15 C16 C17 121.7(3) . . ?
C17 C16 Cl3 118.8(3) . . ?
C18 C13 S3 119.9(3) . . ?
C18 C13 C14 120.3(3) . . ?
C14 C13 S3 119.6(3) . . ?
C3 C2 C1 120.2(3) . . ?
C2 C3 C4 119.3(3) . . ?
C3 C4 Cl1 119.5(3) . . ?
C3 C4 C5 121.4(3) . . ?
C5 C4 Cl1 119.1(3) . . ?
C17 C18 C13 120.0(3) . . ?
C5 C6 C1 120.2(3) . . ?
C6 C5 C4 119.1(3) . . ?
C14 C15 C16 119.2(4) . . ?
C15 C14 C13 120.0(3) . . ?
C18 C17 C16 118.8(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
