# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_jmb002_0m_Compound_3
_database_code_depnum_ccdc_archive 'CCDC 1427394'
_audit_update_record             
;
2015-11-25 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 F2 N P, C F3 O3 S, C H2 Cl2'
_chemical_formula_sum            'C20 H19 Cl2 F5 N O3 P S'
_chemical_formula_weight         550.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0033 0.0016 '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'
F F 0.0171 0.0103 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   9.2119(6)
_cell_length_b                   23.8207(15)
_cell_length_c                   11.1023(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.486(3)
_cell_angle_gamma                90.00
_cell_volume                     2347.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9882
_cell_measurement_theta_min      5.120
_cell_measurement_theta_max      65.036

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.557
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1120
_exptl_absorpt_coefficient_mu    0.497
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6802
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   
'SADABS. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33578
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         32.49
_reflns_number_total             8440
_reflns_number_gt                7219
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'Bruker SMART. Area-Detector Software Package. (Siemens Industrial Automation, 1993, Inc.: Madison, WI)'
_computing_cell_refinement       
'Bruker SMART. Area-Detector Software Package. (Siemens Industrial Automation, 1993, Inc.: Madison, WI)'
_computing_data_reduction        
'Bruker SAINT. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'
_computing_structure_solution    
'SHELX-97. Programs for Crystal Structure Analysis. (G. M. Sheldrick, 1997, Release 97-2, University of Göttingen, Germany)'
_computing_structure_refinement  
'SHELX-97. Programs for Crystal Structure Analysis. (G. M. Sheldrick, 1997, Release 97-2, University of Göttingen, Germany)'
_computing_molecular_graphics    
'Ortep for Windows (L. J. Farrugia, J. Appl. Cryst. 1997, 30, 565)'
_computing_publication_material  
'WinGX v1.70.01 (L. J. Farrugia, J. Appl. Cryst. 1999, 32, 837)'


_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.
;

_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)+(0.0559P)²+1.6759P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8440
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0444
_refine_ls_wR_factor_ref         0.1192
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.30220(14) 0.17164(5) 0.17369(11) 0.0173(2) Uani 1 1 d . . .
C2 C 0.22106(16) 0.19632(6) 0.24877(13) 0.0214(2) Uani 1 1 d . . .
H2 H 0.2384 0.1849 0.3334 0.026 Uiso 1 1 calc R . .
C3 C 0.11433(17) 0.23773(6) 0.20063(14) 0.0245(3) Uani 1 1 d . . .
H3 H 0.0574 0.2541 0.2514 0.029 Uiso 1 1 calc R . .
C4 C 0.09238(17) 0.25473(6) 0.07745(14) 0.0261(3) Uani 1 1 d . . .
H4 H 0.0189 0.2824 0.0423 0.031 Uiso 1 1 calc R . .
C5 C 0.17879(17) 0.23092(6) 0.00686(13) 0.0238(3) Uani 1 1 d . . .
H5 H 0.1667 0.2434 -0.0765 0.029 Uiso 1 1 calc R . .
C6 C 0.36937(18) 0.16774(7) -0.02908(13) 0.0268(3) Uani 1 1 d . . .
H6A H 0.4387 0.1387 0.0152 0.040 Uiso 1 1 calc R . .
H6B H 0.4271 0.1983 -0.0533 0.040 Uiso 1 1 calc R . .
H6C H 0.3009 0.1515 -0.1041 0.040 Uiso 1 1 calc R . .
C7 C 0.58523(14) 0.08435(5) 0.20047(12) 0.0186(2) Uani 1 1 d . . .
C8 C 0.71797(16) 0.11596(6) 0.22593(14) 0.0243(3) Uani 1 1 d . . .
H8 H 0.7206 0.1526 0.2602 0.029 Uiso 1 1 calc R . .
C9 C 0.84635(17) 0.09333(8) 0.20063(16) 0.0313(3) Uani 1 1 d . . .
H9 H 0.9359 0.1151 0.2156 0.038 Uiso 1 1 calc R . .
C10 C 0.84408(18) 0.03913(8) 0.15368(15) 0.0320(3) Uani 1 1 d . . .
H10 H 0.9325 0.0238 0.1381 0.038 Uiso 1 1 calc R . .
C11 C 0.71360(19) 0.00754(7) 0.12961(15) 0.0296(3) Uani 1 1 d . . .
H11 H 0.7129 -0.0296 0.0982 0.036 Uiso 1 1 calc R . .
C12 C 0.58349(17) 0.02993(6) 0.15117(13) 0.0235(2) Uani 1 1 d . . .
H12 H 0.4934 0.0084 0.1326 0.028 Uiso 1 1 calc R . .
C13 C 0.34969(14) 0.06863(5) 0.35052(12) 0.0182(2) Uani 1 1 d . . .
C14 C 0.40389(19) 0.07857(6) 0.47930(13) 0.0268(3) Uani 1 1 d . . .
H14 H 0.4763 0.1073 0.5087 0.032 Uiso 1 1 calc R . .
C15 C 0.3521(2) 0.04659(7) 0.56411(15) 0.0336(3) Uani 1 1 d . . .
H15 H 0.3890 0.0539 0.6511 0.040 Uiso 1 1 calc R . .
C16 C 0.2477(2) 0.00430(7) 0.52344(16) 0.0327(3) Uani 1 1 d . . .
H16 H 0.2123 -0.0172 0.5819 0.039 Uiso 1 1 calc R . .
C17 C 0.1952(2) -0.00632(8) 0.39653(18) 0.0375(4) Uani 1 1 d . . .
H17 H 0.1240 -0.0355 0.3680 0.045 Uiso 1 1 calc R . .
C18 C 0.24559(18) 0.02532(7) 0.31041(15) 0.0298(3) Uani 1 1 d . . .
H18 H 0.2090 0.0174 0.2237 0.036 Uiso 1 1 calc R . .
C19 C -0.4606(2) 0.33890(8) 0.0553(2) 0.0393(4) Uani 1 1 d . . .
C20 C 0.3300(2) 0.35009(9) 0.3773(2) 0.0500(5) Uani 1 1 d . . .
H20A H 0.3227 0.3283 0.4515 0.060 Uiso 1 1 calc R . .
H20B H 0.3500 0.3233 0.3156 0.060 Uiso 1 1 calc R . .
N1 N 0.28070(13) 0.19005(5) 0.05414(10) 0.0189(2) Uani 1 1 d . . .
O1 O -0.3313(2) 0.24991(6) 0.00298(13) 0.0481(4) Uani 1 1 d . . .
O2 O -0.18887(15) 0.31041(6) 0.16738(14) 0.0430(3) Uani 1 1 d . . .
O3 O -0.39588(18) 0.25409(6) 0.20113(12) 0.0416(3) Uani 1 1 d . . .
F1 F 0.30777(9) 0.07464(3) 0.11732(7) 0.02132(16) Uani 1 1 d . . .
F2 F 0.51716(9) 0.15220(3) 0.34789(7) 0.01950(15) Uani 1 1 d . . .
F3 F -0.59890(16) 0.32007(9) 0.0105(2) 0.1103(9) Uani 1 1 d . . .
F4 F -0.4583(3) 0.37568(7) 0.14672(18) 0.0900(7) Uani 1 1 d . . .
F5 F -0.42583(14) 0.36764(5) -0.03558(12) 0.0468(3) Uani 1 1 d . . .
P1 P 0.41765(4) 0.109498(13) 0.23907(3) 0.01590(7) Uani 1 1 d . . .
S1 S -0.32932(4) 0.281997(15) 0.11312(3) 0.02443(8) Uani 1 1 d . . .
Cl1 Cl 0.15693(6) 0.38353(3) 0.31222(7) 0.06329(18) Uani 1 1 d . . .
Cl2 Cl 0.48163(5) 0.39677(2) 0.42191(5) 0.04217(11) Uani 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
C1 N1 1.3612(16) . ?
C1 C2 1.3899(18) . ?
C1 P1 1.8539(13) . ?
C2 C3 1.3946(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.3571(18) . ?
C5 H5 0.9500 . ?
C6 N1 1.4854(18) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 C8 1.3992(19) . ?
C7 C12 1.4054(18) . ?
C7 P1 1.8108(13) . ?
C8 C9 1.395(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.390(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(2) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.3980(19) . ?
C13 C14 1.4030(19) . ?
C13 P1 1.8123(13) . ?
C14 C15 1.391(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.391(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 F3 1.317(2) . ?
C19 F5 1.327(2) . ?
C19 F4 1.337(3) . ?
C19 S1 1.8157(18) . ?
C20 Cl2 1.750(2) . ?
C20 Cl1 1.756(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
O1 S1 1.4380(13) . ?
O2 S1 1.4418(15) . ?
O3 S1 1.4466(13) . ?
F1 P1 1.6765(8) . ?
F2 P1 1.6562(8) . ?

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
N1 C1 C2 119.14(11) . . ?
N1 C1 P1 123.91(9) . . ?
C2 C1 P1 116.56(9) . . ?
C1 C2 C3 120.42(12) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 119.09(13) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 119.04(13) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
N1 C5 C4 121.31(12) . . ?
N1 C5 H5 119.3 . . ?
C4 C5 H5 119.3 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C8 C7 C12 119.57(12) . . ?
C8 C7 P1 121.90(10) . . ?
C12 C7 P1 118.39(10) . . ?
C9 C8 C7 119.57(14) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C10 C9 C8 120.38(15) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 120.21(14) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.21(14) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C11 C12 C7 120.02(14) . . ?
C11 C12 H12 120.0 . . ?
C7 C12 H12 120.0 . . ?
C18 C13 C14 118.44(13) . . ?
C18 C13 P1 120.77(11) . . ?
C14 C13 P1 120.76(10) . . ?
C15 C14 C13 120.31(14) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 120.82(15) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 119.25(15) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 120.67(15) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C13 120.49(15) . . ?
C17 C18 H18 119.8 . . ?
C13 C18 H18 119.8 . . ?
F3 C19 F5 107.13(18) . . ?
F3 C19 F4 109.1(2) . . ?
F5 C19 F4 106.32(17) . . ?
F3 C19 S1 111.41(15) . . ?
F5 C19 S1 112.40(13) . . ?
F4 C19 S1 110.28(15) . . ?
Cl2 C20 Cl1 113.36(12) . . ?
Cl2 C20 H20A 108.9 . . ?
Cl1 C20 H20A 108.9 . . ?
Cl2 C20 H20B 108.9 . . ?
Cl1 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C5 N1 C1 120.92(12) . . ?
C5 N1 C6 117.04(11) . . ?
C1 N1 C6 122.02(11) . . ?
F2 P1 F1 171.79(4) . . ?
F2 P1 C7 92.01(5) . . ?
F1 P1 C7 90.84(5) . . ?
F2 P1 C13 93.25(5) . . ?
F1 P1 C13 92.30(5) . . ?
C7 P1 C13 117.10(6) . . ?
F2 P1 C1 86.74(5) . . ?
F1 P1 C1 85.42(5) . . ?
C7 P1 C1 127.43(6) . . ?
C13 P1 C1 115.44(6) . . ?
O1 S1 O2 114.27(10) . . ?
O1 S1 O3 114.75(9) . . ?
O2 S1 O3 115.36(9) . . ?
O1 S1 C19 103.88(10) . . ?
O2 S1 C19 103.65(9) . . ?
O3 S1 C19 102.69(8) . . ?

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
N1 C1 C2 C3 2.7(2) . . . . ?
P1 C1 C2 C3 -170.38(11) . . . . ?
C1 C2 C3 C4 -1.3(2) . . . . ?
C2 C3 C4 C5 -1.2(2) . . . . ?
C3 C4 C5 N1 2.2(2) . . . . ?
C12 C7 C8 C9 0.8(2) . . . . ?
P1 C7 C8 C9 176.47(12) . . . . ?
C7 C8 C9 C10 -1.8(2) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C9 C10 C11 C12 0.6(2) . . . . ?
C10 C11 C12 C7 -1.6(2) . . . . ?
C8 C7 C12 C11 0.9(2) . . . . ?
P1 C7 C12 C11 -174.96(11) . . . . ?
C18 C13 C14 C15 -1.3(2) . . . . ?
P1 C13 C14 C15 -179.35(13) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C14 C15 C16 C17 0.4(3) . . . . ?
C15 C16 C17 C18 -0.5(3) . . . . ?
C16 C17 C18 C13 -0.3(3) . . . . ?
C14 C13 C18 C17 1.2(2) . . . . ?
P1 C13 C18 C17 179.25(14) . . . . ?
C4 C5 N1 C1 -0.8(2) . . . . ?
C4 C5 N1 C6 -179.24(14) . . . . ?
C2 C1 N1 C5 -1.72(19) . . . . ?
P1 C1 N1 C5 170.85(10) . . . . ?
C2 C1 N1 C6 176.67(13) . . . . ?
P1 C1 N1 C6 -10.76(18) . . . . ?
C8 C7 P1 F2 -23.17(12) . . . . ?
C12 C7 P1 F2 152.57(11) . . . . ?
C8 C7 P1 F1 149.14(11) . . . . ?
C12 C7 P1 F1 -35.12(11) . . . . ?
C8 C7 P1 C13 -117.85(12) . . . . ?
C12 C7 P1 C13 57.89(12) . . . . ?
C8 C7 P1 C1 64.26(14) . . . . ?
C12 C7 P1 C1 -120.00(11) . . . . ?
C18 C13 P1 F2 175.85(12) . . . . ?
C14 C13 P1 F2 -6.17(12) . . . . ?
C18 C13 P1 F1 1.90(12) . . . . ?
C14 C13 P1 F1 179.88(12) . . . . ?
C18 C13 P1 C7 -90.23(13) . . . . ?
C14 C13 P1 C7 87.76(13) . . . . ?
C18 C13 P1 C1 87.92(13) . . . . ?
C14 C13 P1 C1 -94.10(12) . . . . ?
N1 C1 P1 F2 123.17(11) . . . . ?
C2 C1 P1 F2 -64.09(11) . . . . ?
N1 C1 P1 F1 -54.42(11) . . . . ?
C2 C1 P1 F1 118.33(11) . . . . ?
N1 C1 P1 C7 33.13(14) . . . . ?
C2 C1 P1 C7 -154.12(10) . . . . ?
N1 C1 P1 C13 -144.79(11) . . . . ?
C2 C1 P1 C13 27.96(12) . . . . ?
F3 C19 S1 O1 65.1(2) . . . . ?
F5 C19 S1 O1 -55.16(17) . . . . ?
F4 C19 S1 O1 -173.60(15) . . . . ?
F3 C19 S1 O2 -175.20(18) . . . . ?
F5 C19 S1 O2 64.55(17) . . . . ?
F4 C19 S1 O2 -53.89(17) . . . . ?
F3 C19 S1 O3 -54.8(2) . . . . ?
F5 C19 S1 O3 -175.01(15) . . . . ?
F4 C19 S1 O3 66.54(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        32.49
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.148
_refine_diff_density_min         -0.815
_refine_diff_density_rms         0.077
####################################################################### 
# 
# 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_jmb005_0m_Compound_4
_database_code_depnum_ccdc_archive 'CCDC 1427395'
_audit_update_record             
;
2015-11-25 deposited with the CCDC.
2015-12-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 F N P, 2(C F3 O3 S)'
_chemical_formula_sum            'C20 H17 F7 N O6 P S2'
_chemical_formula_weight         595.44

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'
F F 0.0171 0.0103 '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'

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

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

_cell_length_a                   8.157(5)
_cell_length_b                   11.063(5)
_cell_length_c                   14.545(5)
_cell_angle_alpha                71.127(5)
_cell_angle_beta                 77.393(5)
_cell_angle_gamma                84.080(5)
_cell_volume                     1211.3(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9286
_cell_measurement_theta_min      5.120
_cell_measurement_theta_max      65.118

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             604
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7201
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_process_details   
'SADABS. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Apex II CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32906
_diffrn_reflns_av_R_equivalents  0.0300
_diffrn_reflns_av_unetI/netI     0.0275
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.51
_diffrn_reflns_theta_max         32.63
_reflns_number_total             8762
_reflns_number_gt                7220
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'Bruker SMART. Area-Detector Software Package. (Siemens Industrial Automation, 1993, Inc.: Madison, WI)'
_computing_cell_refinement       
'Bruker SMART. Area-Detector Software Package. (Siemens Industrial Automation, 1993, Inc.: Madison, WI)'
_computing_data_reduction        
'Bruker SAINT. Area-Detector Integration Software. (Siemens Industrial Automation, 1995, Inc.: Madison, WI)'
_computing_structure_solution    
'SHELX-97. Programs for Crystal Structure Analysis. (G. M. Sheldrick, 1997, Release 97-2, University of Göttingen, Germany)'
_computing_structure_refinement  
'SHELX-97. Programs for Crystal Structure Analysis. (G. M. Sheldrick, 1997, Release 97-2, University of Göttingen, Germany)'
_computing_molecular_graphics    
'Ortep for Windows (L. J. Farrugia, J. Appl. Cryst. 1997, 30, 565)'
_computing_publication_material  
'WinGX v1.70.01 (L. J. Farrugia, J. Appl. Cryst. 1999, 32, 837)'

_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.
;

_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)+(0.0529P)²+0.6134P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8762
_refine_ls_number_parameters     335
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1016
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.57092(14) 0.82580(10) 0.76661(9) 0.0158(2) Uani 1 1 d . . .
C2 C 0.73676(15) 0.82836(12) 0.71895(9) 0.0186(2) Uani 1 1 d . . .
H2 H 0.7865 0.7586 0.6997 0.022 Uiso 1 1 calc R . .
C3 C 0.82998(16) 0.93591(13) 0.69965(10) 0.0228(2) Uani 1 1 d . . .
H3 H 0.9419 0.9387 0.6673 0.027 Uiso 1 1 calc R . .
C4 C 0.75381(17) 1.03761(12) 0.72928(11) 0.0246(3) Uani 1 1 d . . .
H4 H 0.8144 1.1094 0.7182 0.030 Uiso 1 1 calc R . .
C5 C 0.58619(17) 1.03220(12) 0.77575(10) 0.0218(2) Uani 1 1 d . . .
H5 H 0.5345 1.1014 0.7951 0.026 Uiso 1 1 calc R . .
C6 C 0.31877(17) 0.93121(13) 0.84344(11) 0.0264(3) Uani 1 1 d . . .
H6A H 0.3068 0.8773 0.9110 0.040 Uiso 1 1 calc R . .
H6B H 0.2511 0.9005 0.8099 0.040 Uiso 1 1 calc R . .
H6C H 0.2827 1.0171 0.8419 0.040 Uiso 1 1 calc R . .
C7 C 0.60177(16) 0.55481(11) 0.78760(10) 0.0196(2) Uani 1 1 d . . .
C8 C 0.69816(19) 0.51298(13) 0.86176(11) 0.0269(3) Uani 1 1 d . . .
H8 H 0.6826 0.5504 0.9120 0.032 Uiso 1 1 calc R . .
C9 C 0.8174(2) 0.41445(15) 0.85863(13) 0.0330(3) Uani 1 1 d . . .
H9 H 0.8825 0.3853 0.9071 0.040 Uiso 1 1 calc R . .
C10 C 0.8395(2) 0.35934(14) 0.78321(13) 0.0332(3) Uani 1 1 d . . .
H10 H 0.9195 0.2934 0.7817 0.040 Uiso 1 1 calc R . .
C11 C 0.7437(2) 0.40135(14) 0.71004(12) 0.0307(3) Uani 1 1 d . . .
H11 H 0.7600 0.3636 0.6600 0.037 Uiso 1 1 calc R . .
C12 C 0.62371(18) 0.49965(12) 0.71152(11) 0.0248(3) Uani 1 1 d . . .
H12 H 0.5590 0.5283 0.6628 0.030 Uiso 1 1 calc R . .
C13 C 0.32335(15) 0.71343(11) 0.70221(9) 0.0179(2) Uani 1 1 d . . .
C14 C 0.20212(17) 0.62420(12) 0.71638(11) 0.0254(3) Uani 1 1 d . . .
H14 H 0.1878 0.5523 0.7721 0.031 Uiso 1 1 calc R . .
C15 C 0.10463(18) 0.64586(14) 0.64541(12) 0.0288(3) Uani 1 1 d . . .
H15 H 0.0233 0.5882 0.6537 0.035 Uiso 1 1 calc R . .
C16 C 0.12721(18) 0.75331(16) 0.56170(12) 0.0289(3) Uani 1 1 d . . .
H16 H 0.0619 0.7663 0.5141 0.035 Uiso 1 1 calc R . .
C17 C 0.24642(18) 0.84102(15) 0.54889(11) 0.0292(3) Uani 1 1 d . . .
H17 H 0.2596 0.9131 0.4932 0.035 Uiso 1 1 calc R . .
C18 C 0.34612(16) 0.82173(13) 0.61873(10) 0.0226(2) Uani 1 1 d . . .
H18 H 0.4269 0.8800 0.6101 0.027 Uiso 1 1 calc R . .
C19 C 0.7042(3) 0.66156(16) 0.41804(14) 0.0442(4) Uani 1 1 d . . .
C20 C 0.8580(2) 0.83919(16) 0.98578(13) 0.0359(4) Uani 1 1 d . . .
N1 N 0.49711(13) 0.92921(9) 0.79334(8) 0.01746(18) Uani 1 1 d . . .
O1 O 0.90371(17) 0.84727(18) 0.35949(11) 0.0568(4) Uani 1 1 d . . .
O2 O 0.60396(17) 0.89524(12) 0.38079(10) 0.0410(3) Uani 1 1 d . . .
O3 O 0.73200(15) 0.79944(13) 0.52454(9) 0.0368(3) Uani 1 1 d . . .
O4 O 0.6028(2) 0.77529(14) 1.12578(10) 0.0512(4) Uani 1 1 d . . .
O5 O 0.59599(15) 0.74639(11) 0.96857(9) 0.0350(3) Uani 1 1 d . . .
O6 O 0.77265(17) 0.60691(10) 1.07532(10) 0.0411(3) Uani 1 1 d . . .
F5 F 0.95506(16) 0.80889(15) 0.90956(11) 0.0665(4) Uani 1 1 d . . .
F1 F 0.34765(10) 0.65481(7) 0.89278(6) 0.02275(16) Uani 1 1 d . . .
F2 F 0.7172(2) 0.65918(14) 0.32612(10) 0.0698(4) Uani 1 1 d . . .
F3 F 0.8151(3) 0.57603(14) 0.45919(12) 0.0920(7) Uani 1 1 d . . .
F4 F 0.5516(2) 0.62426(14) 0.46866(12) 0.0816(5) Uani 1 1 d . . .
F6 F 0.79998(17) 0.95915(10) 0.95035(10) 0.0544(3) Uani 1 1 d . . .
F7 F 0.95524(17) 0.84060(12) 1.04804(11) 0.0630(4) Uani 1 1 d . . .
P1 P 0.45664(4) 0.68392(3) 0.78791(2) 0.01640(7) Uani 1 1 d . . .
S1 S 0.74033(4) 0.81888(3) 0.42095(3) 0.02342(8) Uani 1 1 d . . .
S2 S 0.68702(4) 0.72942(3) 1.04612(2) 0.02042(7) Uani 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
C1 N1 1.3659(16) . ?
C1 C2 1.3774(18) . ?
C1 P1 1.8138(13) . ?
C2 C3 1.3965(18) . ?
C2 H2 0.9300 . ?
C3 C4 1.375(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(2) . ?
C4 H4 0.9300 . ?
C5 N1 1.3389(16) . ?
C5 H5 0.9300 . ?
C6 N1 1.4794(18) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 C12 1.3989(19) . ?
C7 C8 1.4029(19) . ?
C7 P1 1.7592(14) . ?
C8 C9 1.389(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.390(2) . ?
C9 H9 0.9300 . ?
C10 C11 1.388(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(2) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.3967(18) . ?
C13 C14 1.4056(18) . ?
C13 P1 1.7600(14) . ?
C14 C15 1.384(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.393(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.386(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.387(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 F2 1.327(2) . ?
C19 F3 1.328(2) . ?
C19 F4 1.331(3) . ?
C19 S1 1.8101(19) . ?
C20 F5 1.331(2) . ?
C20 F7 1.332(2) . ?
C20 F6 1.336(2) . ?
C20 S2 1.8209(18) . ?
O1 S1 1.4348(15) . ?
O2 S1 1.4362(13) . ?
O3 S1 1.4385(13) . ?
O4 S2 1.4258(13) . ?
O5 S2 1.4348(12) . ?
O6 S2 1.4377(12) . ?
F1 P1 1.5395(10) . ?

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
N1 C1 C2 120.00(11) . . ?
N1 C1 P1 122.44(9) . . ?
C2 C1 P1 117.53(9) . . ?
C1 C2 C3 119.87(12) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 118.99(12) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C3 C4 C5 119.45(12) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 121.27(12) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C12 C7 C8 121.44(12) . . ?
C12 C7 P1 119.55(10) . . ?
C8 C7 P1 118.95(10) . . ?
C9 C8 C7 118.59(14) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
C10 C9 C8 120.15(14) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.93(14) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C12 C11 C10 120.05(15) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C7 118.85(13) . . ?
C11 C12 H12 120.6 . . ?
C7 C12 H12 120.6 . . ?
C18 C13 C14 121.30(12) . . ?
C18 C13 P1 119.25(10) . . ?
C14 C13 P1 119.37(10) . . ?
C15 C14 C13 118.44(13) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C16 120.59(13) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C17 C16 C15 120.42(13) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C18 120.27(14) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 118.98(13) . . ?
C17 C18 H18 120.5 . . ?
C13 C18 H18 120.5 . . ?
F2 C19 F3 107.79(18) . . ?
F2 C19 F4 108.29(18) . . ?
F3 C19 F4 107.58(18) . . ?
F2 C19 S1 111.78(13) . . ?
F3 C19 S1 110.73(16) . . ?
F4 C19 S1 110.52(14) . . ?
F5 C20 F7 107.96(16) . . ?
F5 C20 F6 106.95(15) . . ?
F7 C20 F6 106.66(14) . . ?
F5 C20 S2 111.59(13) . . ?
F7 C20 S2 111.95(12) . . ?
F6 C20 S2 111.46(13) . . ?
C5 N1 C1 120.40(11) . . ?
C5 N1 C6 117.81(11) . . ?
C1 N1 C6 121.79(10) . . ?
F1 P1 C7 107.56(6) . . ?
F1 P1 C13 108.57(7) . . ?
C7 P1 C13 114.69(6) . . ?
F1 P1 C1 106.74(5) . . ?
C7 P1 C1 108.70(7) . . ?
C13 P1 C1 110.26(6) . . ?
O1 S1 O2 115.01(10) . . ?
O1 S1 O3 114.93(9) . . ?
O2 S1 O3 114.97(8) . . ?
O1 S1 C19 103.49(11) . . ?
O2 S1 C19 102.87(9) . . ?
O3 S1 C19 103.15(8) . . ?
O4 S2 O5 115.70(10) . . ?
O4 S2 O6 115.06(9) . . ?
O5 S2 O6 114.49(8) . . ?
O4 S2 C20 102.83(10) . . ?
O5 S2 C20 102.85(8) . . ?
O6 S2 C20 103.36(9) . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        32.63
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.522
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.066
