# 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_20170307caochengyao1
_database_code_depnum_ccdc_archive 'CCDC 1914419'
loop_
_audit_author_name
_audit_author_address
'Chengyao Cao'
;Tsinghua University
China
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-07-09 downloaded from the CCDC.
;
_audit_creation_date             2019-04-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H18 F3 O2 P S'
_chemical_formula_sum            'C22 H18 F3 O2 P S'
_chemical_formula_weight         434.39
_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 0.0181 0.0091 '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'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7335(2)
_cell_length_b                   20.6854(3)
_cell_length_c                   10.7411(2)
_cell_angle_alpha                90
_cell_angle_beta                 103.192(2)
_cell_angle_gamma                90
_cell_volume                     2105.56(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6891
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      76.4010
_cell_measurement_theta_min      4.7270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.459
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25072
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10455
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.704
_diffrn_reflns_theta_min         4.275
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -47.00 -16.00   1.00    1.00    --  -40.81 -57.00 -60.00   31
  2  ω    -61.00  31.00   1.00    1.00    --  -40.81  57.00  90.00   92
  3  ω     82.00 115.00   1.00    1.00    --   40.81  38.00-150.00   33
  4  ω     81.00 106.00   1.00    1.00    --  112.00  77.00 -30.00   25
  5  ω     87.00 171.00   1.00    1.00    --  112.00  61.00   0.00   84
  6  ω    132.00 175.00   1.00    1.00    --  112.00  77.00 -30.00   43
  7  ω    147.00 175.00   1.00    1.00    --  112.00  45.00-120.00   28
  8  ω     90.00 163.00   1.00    1.00    --  112.00  45.00 -30.00   73
  9  ω    130.00 166.00   1.00    1.00    --  112.00 111.00 120.00   36
 10  ω     88.00 177.00   1.00    1.00    --  112.00  45.00 -90.00   89
 11  ω     44.00 115.00   1.00    1.00    --  112.00-111.00 120.00   71
 12  ω     24.00  59.00   1.00    1.00    --   40.81-125.00 -30.00   35
 13  ω     30.00  75.00   1.00    1.00    --  112.00 -95.00 -90.00   45
 14  ω     37.00 107.00   1.00    1.00    --  112.00 -95.00 -60.00   70
 15  ω     38.00  71.00   1.00    1.00    --  112.00-111.00-180.00   33
 16  ω   -110.00 -64.00   1.00    1.00    --  -40.81 -57.00 -60.00   46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0945245000
_diffrn_orient_matrix_UB_12      -0.0353447000
_diffrn_orient_matrix_UB_13      -0.1143398000
_diffrn_orient_matrix_UB_21      -0.1137954000
_diffrn_orient_matrix_UB_22      0.0525866000
_diffrn_orient_matrix_UB_23      -0.0079472000
_diffrn_orient_matrix_UB_31      0.0674337000
_diffrn_orient_matrix_UB_32      0.0391363000
_diffrn_orient_matrix_UB_33      -0.0925492000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3997
_reflns_number_total             4378
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     74.33
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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         0.566
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         4378
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0404
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1407
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00C(H00C), C00D(H00D), C00F(H00F), C00G(H00G), C00H(H00H), C00I(H00I),
 C00J(H00J), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q),
 C00R(H00R), C00S(H00S), C00T(H00T)
2.b Idealised Me refined as rotating group:
 C00M(H00a,H00b,H00e)
;
_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
P001 P 0.74843(4) 0.42088(2) 0.31180(3) 0.02289(14) Uani 1 1 d . . . . .
S002 S 1.03989(4) 0.36447(2) 0.40701(3) 0.02912(15) Uani 1 1 d . . . . .
O003 O 0.83490(13) 0.42490(6) 0.06898(11) 0.0332(3) Uani 1 1 d . . . . .
O004 O 1.06159(13) 0.39420(6) 0.14548(11) 0.0327(3) Uani 1 1 d . . . . .
F005 F 0.89315(15) 0.25591(6) 0.39972(14) 0.0581(4) Uani 1 1 d . . . . .
F006 F 1.01567(18) 0.26003(7) 0.26129(15) 0.0671(4) Uani 1 1 d . . . . .
F007 F 1.1184(2) 0.24729(8) 0.4570(2) 0.1045(8) Uani 1 1 d . . . . .
C008 C 0.92937(16) 0.40682(8) 0.15900(14) 0.0265(3) Uani 1 1 d . . . . .
C009 C 0.91063(16) 0.39705(7) 0.28607(14) 0.0243(3) Uani 1 1 d . . . . .
C00A C 0.70055(17) 0.50009(7) 0.24554(14) 0.0261(3) Uani 1 1 d . . . . .
C00B C 0.75672(17) 0.42613(8) 0.48162(15) 0.0284(3) Uani 1 1 d . . . . .
C00C C 0.80340(19) 0.54873(8) 0.27264(15) 0.0311(3) Uani 1 1 d . . . . .
H00C H 0.8942 0.5392 0.3187 0.037 Uiso 1 1 calc R . . . .
C00D C 0.56588(19) 0.51425(9) 0.17338(16) 0.0329(3) Uani 1 1 d . . . . .
H00D H 0.4976 0.4820 0.1554 0.039 Uiso 1 1 calc R . . . .
C00E C 0.60640(17) 0.36506(8) 0.25091(17) 0.0312(4) Uani 1 1 d . . . . .
C00F C 0.76172(18) 0.48536(9) 0.54265(16) 0.0336(4) Uani 1 1 d . . . . .
H00F H 0.7580 0.5234 0.4958 0.040 Uiso 1 1 calc R . . . .
C00G C 0.7685(2) 0.61133(8) 0.23002(17) 0.0385(4) Uani 1 1 d . . . . .
H00G H 0.8353 0.6441 0.2499 0.046 Uiso 1 1 calc R . . . .
C00H C 0.6248(2) 0.31662(9) 0.16602(19) 0.0408(4) Uani 1 1 d . . . . .
H00H H 0.7076 0.3144 0.1370 0.049 Uiso 1 1 calc R . . . .
C00I C 0.7753(2) 0.43167(11) 0.74406(17) 0.0420(4) Uani 1 1 d . . . . .
H00I H 0.7816 0.4335 0.8317 0.050 Uiso 1 1 calc R . . . .
C00J C 0.6344(2) 0.62503(9) 0.15797(18) 0.0413(4) Uani 1 1 d . . . . .
H00J H 0.6119 0.6670 0.1294 0.050 Uiso 1 1 calc R . . . .
C00K C 1.0146(2) 0.27872(9) 0.3806(2) 0.0424(4) Uani 1 1 d . . . . .
C00L C 0.5340(2) 0.57687(9) 0.12824(19) 0.0412(4) Uani 1 1 d . . . . .
H00L H 0.4450 0.5863 0.0781 0.049 Uiso 1 1 calc R . . . .
C00M C 1.0879(2) 0.40616(10) 0.02126(17) 0.0407(4) Uani 1 1 d . . . . .
H00A H 1.0236 0.3811 -0.0415 0.061 Uiso 1 1 calc GR . . . .
H00B H 1.1831 0.3941 0.0211 0.061 Uiso 1 1 calc GR . . . .
H00E H 1.0744 0.4513 0.0011 0.061 Uiso 1 1 calc GR . . . .
C00N C 0.7723(2) 0.48805(11) 0.67418(17) 0.0400(4) Uani 1 1 d . . . . .
H00N H 0.7774 0.5279 0.7151 0.048 Uiso 1 1 calc R . . . .
C00O C 0.7587(2) 0.36943(9) 0.55249(19) 0.0437(5) Uani 1 1 d . . . . .
H00O H 0.7533 0.3294 0.5121 0.052 Uiso 1 1 calc R . . . .
C00P C 0.7688(3) 0.37284(12) 0.6830(2) 0.0509(5) Uani 1 1 d . . . . .
H00P H 0.7712 0.3349 0.7300 0.061 Uiso 1 1 calc R . . . .
C00Q C 0.4811(2) 0.36825(11) 0.2935(2) 0.0493(5) Uani 1 1 d . . . . .
H00Q H 0.4685 0.4006 0.3499 0.059 Uiso 1 1 calc R . . . .
C00R C 0.5177(3) 0.27159(11) 0.1253(2) 0.0587(6) Uani 1 1 d . . . . .
H00R H 0.5290 0.2392 0.0685 0.070 Uiso 1 1 calc R . . . .
C00S C 0.3945(2) 0.27475(12) 0.1686(3) 0.0677(8) Uani 1 1 d . . . . .
H00S H 0.3239 0.2442 0.1418 0.081 Uiso 1 1 calc R . . . .
C00T C 0.3762(2) 0.32322(14) 0.2516(3) 0.0656(8) Uani 1 1 d . . . . .
H00T H 0.2926 0.3255 0.2795 0.079 Uiso 1 1 calc R . . . .


_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
P001 C009 1.7353(15) . ?
P001 C00A 1.8047(15) . ?
P001 C00B 1.8105(16) . ?
P001 C00E 1.8053(16) . ?
S002 C009 1.7258(15) . ?
S002 C00K 1.804(2) . ?
O003 C008 1.231(2) . ?
O004 C008 1.3530(19) . ?
O004 C00M 1.436(2) . ?
F005 C00K 1.331(2) . ?
F006 C00K 1.341(3) . ?
F007 C00K 1.319(2) . ?
C008 C009 1.432(2) . ?
C00A C00C 1.402(2) . ?
C00A C00D 1.393(2) . ?
C00B C00F 1.385(2) . ?
C00B C00O 1.396(2) . ?
C00C H00C 0.9300 . ?
C00C C00G 1.390(2) . ?
C00D H00D 0.9300 . ?
C00D C00L 1.393(2) . ?
C00E C00H 1.394(3) . ?
C00E C00Q 1.398(3) . ?
C00F H00F 0.9300 . ?
C00F C00N 1.394(2) . ?
C00G H00G 0.9300 . ?
C00G C00J 1.386(3) . ?
C00H H00H 0.9300 . ?
C00H C00R 1.392(3) . ?
C00I H00I 0.9300 . ?
C00I C00N 1.384(3) . ?
C00I C00P 1.377(3) . ?
C00J H00J 0.9300 . ?
C00J C00L 1.381(3) . ?
C00L H00L 0.9300 . ?
C00M H00A 0.9600 . ?
C00M H00B 0.9600 . ?
C00M H00E 0.9600 . ?
C00N H00N 0.9300 . ?
C00O H00O 0.9300 . ?
C00O C00P 1.385(3) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00T 1.379(3) . ?
C00R H00R 0.9300 . ?
C00R C00S 1.383(4) . ?
C00S H00S 0.9300 . ?
C00S C00T 1.380(4) . ?
C00T H00T 0.9300 . ?

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
C009 P001 C00A 110.95(7) . . ?
C009 P001 C00B 110.15(7) . . ?
C009 P001 C00E 114.20(8) . . ?
C00A P001 C00B 106.92(7) . . ?
C00A P001 C00E 109.29(7) . . ?
C00E P001 C00B 104.94(8) . . ?
C009 S002 C00K 102.45(8) . . ?
C008 O004 C00M 116.22(13) . . ?
O003 C008 O004 122.19(14) . . ?
O003 C008 C009 123.84(14) . . ?
O004 C008 C009 113.97(13) . . ?
S002 C009 P001 121.64(9) . . ?
C008 C009 P001 115.47(11) . . ?
C008 C009 S002 122.89(11) . . ?
C00C C00A P001 117.49(12) . . ?
C00D C00A P001 122.40(13) . . ?
C00D C00A C00C 120.08(15) . . ?
C00F C00B P001 121.24(12) . . ?
C00F C00B C00O 119.37(16) . . ?
C00O C00B P001 119.39(13) . . ?
C00A C00C H00C 120.3 . . ?
C00G C00C C00A 119.41(16) . . ?
C00G C00C H00C 120.3 . . ?
C00A C00D H00D 120.1 . . ?
C00L C00D C00A 119.73(17) . . ?
C00L C00D H00D 120.1 . . ?
C00H C00E P001 119.66(14) . . ?
C00H C00E C00Q 119.99(18) . . ?
C00Q C00E P001 120.28(15) . . ?
C00B C00F H00F 119.9 . . ?
C00B C00F C00N 120.10(17) . . ?
C00N C00F H00F 119.9 . . ?
C00C C00G H00G 119.9 . . ?
C00J C00G C00C 120.16(18) . . ?
C00J C00G H00G 119.9 . . ?
C00E C00H H00H 120.4 . . ?
C00R C00H C00E 119.2(2) . . ?
C00R C00H H00H 120.4 . . ?
C00N C00I H00I 120.2 . . ?
C00P C00I H00I 120.2 . . ?
C00P C00I C00N 119.58(16) . . ?
C00G C00J H00J 119.7 . . ?
C00L C00J C00G 120.56(16) . . ?
C00L C00J H00J 119.7 . . ?
F005 C00K S002 114.74(14) . . ?
F005 C00K F006 104.24(17) . . ?
F006 C00K S002 113.77(14) . . ?
F007 C00K S002 109.22(15) . . ?
F007 C00K F005 108.10(19) . . ?
F007 C00K F006 106.3(2) . . ?
C00D C00L H00L 120.0 . . ?
C00J C00L C00D 120.01(18) . . ?
C00J C00L H00L 120.0 . . ?
O004 C00M H00A 109.5 . . ?
O004 C00M H00B 109.5 . . ?
O004 C00M H00E 109.5 . . ?
H00A C00M H00B 109.5 . . ?
H00A C00M H00E 109.5 . . ?
H00B C00M H00E 109.5 . . ?
C00F C00N H00N 119.9 . . ?
C00I C00N C00F 120.24(18) . . ?
C00I C00N H00N 119.9 . . ?
C00B C00O H00O 120.1 . . ?
C00P C00O C00B 119.89(19) . . ?
C00P C00O H00O 120.1 . . ?
C00I C00P C00O 120.80(18) . . ?
C00I C00P H00P 119.6 . . ?
C00O C00P H00P 119.6 . . ?
C00E C00Q H00Q 120.1 . . ?
C00T C00Q C00E 119.8(2) . . ?
C00T C00Q H00Q 120.1 . . ?
C00H C00R H00R 119.8 . . ?
C00S C00R C00H 120.5(2) . . ?
C00S C00R H00R 119.8 . . ?
C00R C00S H00S 119.9 . . ?
C00T C00S C00R 120.1(2) . . ?
C00T C00S H00S 119.9 . . ?
C00Q C00T C00S 120.4(2) . . ?
C00Q C00T H00T 119.8 . . ?
C00S C00T H00T 119.8 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.302
_oxdiff_exptl_absorpt_empirical_full_min 0.461
