# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_pre
_database_code_depnum_ccdc_archive 'CCDC 1471988'
_audit_update_record             
;
2016-04-04 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 Cl10 F5 P'
_chemical_formula_weight         696.69

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'
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'
Cl Cl 0.1484 0.1585 '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

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

_cell_length_a                   8.6247(6)
_cell_length_b                   13.0708(10)
_cell_length_c                   13.2510(10)
_cell_angle_alpha                81.217(4)
_cell_angle_beta                 71.522(4)
_cell_angle_gamma                89.820(4)
_cell_volume                     1398.55(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5189
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      26.99

_exptl_crystal_description       ?rod?
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             706
_exptl_absorpt_coefficient_mu    1.098
_exptl_absorpt_correction_type   ?multi-scan?
_exptl_absorpt_correction_T_min  0.6097
_exptl_absorpt_correction_T_max  0.8102
_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_reflns_number            23824
_diffrn_reflns_av_R_equivalents  0.0697
_diffrn_reflns_av_sigmaI/netI    0.0937
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.58
_diffrn_reflns_theta_max         27.51
_reflns_number_total             6362
_reflns_number_gt                3917
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0457P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   ?none?
_refine_ls_hydrogen_treatment    ?none?
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6362
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1012
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   0.907
_refine_ls_restrained_S_all      0.907
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.003 0.000 337 134 ' '
_platon_squeeze_details          
;
;




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
Cl1 Cl 0.39836(10) 1.18767(6) 0.41719(8) 0.0290(2) Uani 1 1 d . . .
Cl2 Cl 0.07425(9) 1.11460(6) 0.38901(8) 0.0275(2) Uani 1 1 d . . .
Cl3 Cl 0.04549(9) 0.90598(6) 0.31656(8) 0.0262(2) Uani 1 1 d . . .
Cl4 Cl 0.07256(11) 0.67531(8) 0.17826(7) 0.0384(3) Uani 1 1 d . . .
Cl5 Cl -0.25592(10) 0.57236(7) 0.31761(8) 0.0342(2) Uani 1 1 d . . .
Cl6 Cl -0.35876(10) 0.54492(7) 0.56655(8) 0.0363(3) Uani 1 1 d . . .
Cl7 Cl -0.11274(11) 0.60712(7) 0.67786(7) 0.0315(2) Uani 1 1 d . . .
Cl8 Cl 0.22724(10) 0.70819(6) 0.53999(7) 0.0241(2) Uani 1 1 d . . .
Cl9 Cl 0.67920(9) 0.84188(6) 0.28568(8) 0.0282(2) Uani 1 1 d . . .
Cl10 Cl 0.70332(9) 1.05370(7) 0.35911(8) 0.0287(2) Uani 1 1 d . . .
P1 P 0.35953(9) 0.73601(6) 0.29878(7) 0.0171(2) Uani 1 1 d . . .
F1 F 0.6214(3) 0.7408(2) -0.17566(18) 0.0652(8) Uani 1 1 d . . .
F2 F 0.3334(3) 0.91173(16) 0.10525(16) 0.0389(5) Uani 1 1 d . . .
F3 F 0.4670(3) 0.90901(18) -0.10396(18) 0.0545(7) Uani 1 1 d . . .
F4 F 0.5049(3) 0.57180(16) 0.17897(17) 0.0383(5) Uani 1 1 d . . .
C1 C 0.5557(5) 0.7399(4) -0.0694(3) 0.0423(11) Uani 1 1 d . . .
C2 C 0.4794(4) 0.8263(3) -0.0333(3) 0.0345(10) Uani 1 1 d . . .
C3 C 0.4121(4) 0.8261(3) 0.0751(3) 0.0252(8) Uani 1 1 d . . .
C4 C 0.4179(4) 0.7420(2) 0.1520(3) 0.0198(8) Uani 1 1 d . . .
C5 C 0.3584(3) 0.8738(2) 0.3161(3) 0.0162(7) Uani 1 1 d . . .
C6 C 0.2266(3) 0.9390(2) 0.3354(3) 0.0174(7) Uani 1 1 d . . .
C7 C 0.2390(3) 1.0362(2) 0.3656(3) 0.0176(7) Uani 1 1 d . . .
C8 C 0.3853(4) 1.0701(2) 0.3758(3) 0.0186(7) Uani 1 1 d . . .
C9 C 0.5642(5) 0.6552(3) 0.0026(3) 0.0372(10) Uani 1 1 d . . .
F5 F 0.6410(3) 0.57217(19) -0.0340(2) 0.0595(7) Uani 1 1 d . . .
C11 C 0.4957(4) 0.6567(3) 0.1107(3) 0.0269(8) Uani 1 1 d . . .
C12 C 0.1434(3) 0.6877(2) 0.3627(3) 0.0172(7) Uani 1 1 d . . .
C13 C 0.0315(4) 0.6560(2) 0.3159(3) 0.0204(8) Uani 1 1 d . . .
C14 C -0.1217(4) 0.6108(2) 0.3788(3) 0.0217(8) Uani 1 1 d . . .
C15 C -0.1681(4) 0.5975(2) 0.4901(3) 0.0232(8) Uani 1 1 d . . .
C16 C -0.0592(4) 0.6265(2) 0.5396(3) 0.0207(8) Uani 1 1 d . . .
C17 C 0.0945(4) 0.6703(2) 0.4762(3) 0.0174(7) Uani 1 1 d . . .
C18 C 0.5068(3) 0.9139(2) 0.3213(3) 0.0172(7) Uani 1 1 d . . .
C19 C 0.5204(4) 1.0101(2) 0.3513(3) 0.0192(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
Cl1 C8 1.724(3) . ?
Cl2 C7 1.724(3) . ?
Cl3 C6 1.724(3) . ?
Cl4 C13 1.722(4) . ?
Cl5 C14 1.724(3) . ?
Cl6 C15 1.715(3) . ?
Cl7 C16 1.720(3) . ?
Cl8 C17 1.737(3) . ?
Cl9 C18 1.733(3) . ?
Cl10 C19 1.719(3) . ?
P1 C4 1.837(3) . ?
P1 C5 1.850(3) . ?
P1 C12 1.853(3) . ?
F1 C1 1.339(4) . ?
F2 C3 1.354(4) . ?
F3 C2 1.345(4) . ?
F4 C11 1.340(4) . ?
C1 C2 1.378(5) . ?
C1 C9 1.365(6) . ?
C2 C3 1.368(5) . ?
C3 C4 1.393(5) . ?
C4 C11 1.394(5) . ?
C5 C6 1.400(4) . ?
C5 C18 1.409(4) . ?
C6 C7 1.404(4) . ?
C7 C8 1.391(4) . ?
C8 C19 1.382(4) . ?
C9 F5 1.343(4) . ?
C9 C11 1.368(5) . ?
C12 C13 1.396(4) . ?
C12 C17 1.409(4) . ?
C13 C14 1.395(4) . ?
C14 C15 1.384(5) . ?
C15 C16 1.387(5) . ?
C16 C17 1.394(4) . ?
C18 C19 1.391(4) . ?

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
C4 P1 C5 103.58(15) . . ?
C4 P1 C12 109.85(15) . . ?
C5 P1 C12 104.57(13) . . ?
F1 C1 C2 118.9(4) . . ?
F1 C1 C9 120.9(4) . . ?
C2 C1 C9 120.2(4) . . ?
F3 C2 C3 120.3(4) . . ?
F3 C2 C1 120.4(4) . . ?
C3 C2 C1 119.3(4) . . ?
F2 C3 C2 116.4(3) . . ?
F2 C3 C4 120.6(3) . . ?
C2 C3 C4 122.9(3) . . ?
C11 C4 C3 115.1(3) . . ?
C11 C4 P1 116.4(3) . . ?
C3 C4 P1 128.0(3) . . ?
C6 C5 C18 116.5(3) . . ?
C6 C5 P1 128.5(2) . . ?
C18 C5 P1 114.6(2) . . ?
C5 C6 C7 121.4(3) . . ?
C5 C6 Cl3 121.4(2) . . ?
C7 C6 Cl3 117.1(2) . . ?
C8 C7 C6 119.9(3) . . ?
C8 C7 Cl2 119.8(2) . . ?
C6 C7 Cl2 120.3(2) . . ?
C7 C8 C19 119.9(3) . . ?
C7 C8 Cl1 119.9(2) . . ?
C19 C8 Cl1 120.2(2) . . ?
F5 C9 C11 121.2(4) . . ?
F5 C9 C1 119.3(4) . . ?
C11 C9 C1 119.5(4) . . ?
F4 C11 C9 117.8(3) . . ?
F4 C11 C4 119.1(3) . . ?
C9 C11 C4 123.0(4) . . ?
C13 C12 C17 116.6(3) . . ?
C13 C12 P1 129.7(3) . . ?
C17 C12 P1 113.2(2) . . ?
C12 C13 C14 121.4(3) . . ?
C12 C13 Cl4 121.7(2) . . ?
C14 C13 Cl4 116.8(3) . . ?
C15 C14 C13 120.6(3) . . ?
C15 C14 Cl5 119.5(2) . . ?
C13 C14 Cl5 119.9(3) . . ?
C14 C15 C16 119.6(3) . . ?
C14 C15 Cl6 120.2(3) . . ?
C16 C15 Cl6 120.2(3) . . ?
C15 C16 C17 119.4(3) . . ?
C15 C16 Cl7 120.2(2) . . ?
C17 C16 Cl7 120.4(3) . . ?
C16 C17 C12 122.3(3) . . ?
C16 C17 Cl8 118.5(3) . . ?
C12 C17 Cl8 119.1(2) . . ?
C19 C18 C5 122.4(3) . . ?
C19 C18 Cl9 119.0(2) . . ?
C5 C18 Cl9 118.6(2) . . ?
C18 C19 C8 119.6(3) . . ?
C18 C19 Cl10 120.3(2) . . ?
C8 C19 Cl10 120.1(2) . . ?

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
F1 C1 C2 F3 1.9(6) . . . . ?
C9 C1 C2 F3 -178.3(3) . . . . ?
F1 C1 C2 C3 -179.9(3) . . . . ?
C9 C1 C2 C3 -0.1(6) . . . . ?
F3 C2 C3 F2 0.6(5) . . . . ?
C1 C2 C3 F2 -177.5(3) . . . . ?
F3 C2 C3 C4 178.6(3) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
F2 C3 C4 C11 177.0(3) . . . . ?
C2 C3 C4 C11 -0.9(5) . . . . ?
F2 C3 C4 P1 -11.3(4) . . . . ?
C2 C3 C4 P1 170.8(3) . . . . ?
C5 P1 C4 C11 153.4(2) . . . . ?
C12 P1 C4 C11 -95.4(3) . . . . ?
C5 P1 C4 C3 -18.2(3) . . . . ?
C12 P1 C4 C3 93.1(3) . . . . ?
C4 P1 C5 C6 94.0(3) . . . . ?
C12 P1 C5 C6 -21.1(3) . . . . ?
C4 P1 C5 C18 -93.2(3) . . . . ?
C12 P1 C5 C18 151.8(2) . . . . ?
C18 C5 C6 C7 -4.3(5) . . . . ?
P1 C5 C6 C7 168.5(3) . . . . ?
C18 C5 C6 Cl3 172.5(2) . . . . ?
P1 C5 C6 Cl3 -14.8(4) . . . . ?
C5 C6 C7 C8 0.7(5) . . . . ?
Cl3 C6 C7 C8 -176.2(2) . . . . ?
C5 C6 C7 Cl2 -179.9(2) . . . . ?
Cl3 C6 C7 Cl2 3.2(4) . . . . ?
C6 C7 C8 C19 3.0(5) . . . . ?
Cl2 C7 C8 C19 -176.4(3) . . . . ?
C6 C7 C8 Cl1 -177.9(2) . . . . ?
Cl2 C7 C8 Cl1 2.7(4) . . . . ?
F1 C1 C9 F5 0.6(6) . . . . ?
C2 C1 C9 F5 -179.1(3) . . . . ?
F1 C1 C9 C11 -179.9(3) . . . . ?
C2 C1 C9 C11 0.3(6) . . . . ?
F5 C9 C11 F4 -1.2(5) . . . . ?
C1 C9 C11 F4 179.4(3) . . . . ?
F5 C9 C11 C4 178.6(3) . . . . ?
C1 C9 C11 C4 -0.8(6) . . . . ?
C3 C4 C11 F4 -179.1(3) . . . . ?
P1 C4 C11 F4 8.2(4) . . . . ?
C3 C4 C11 C9 1.0(5) . . . . ?
P1 C4 C11 C9 -171.7(3) . . . . ?
C4 P1 C12 C13 1.5(3) . . . . ?
C5 P1 C12 C13 112.1(3) . . . . ?
C4 P1 C12 C17 173.5(2) . . . . ?
C5 P1 C12 C17 -75.9(3) . . . . ?
C17 C12 C13 C14 0.9(5) . . . . ?
P1 C12 C13 C14 172.7(2) . . . . ?
C17 C12 C13 Cl4 178.3(2) . . . . ?
P1 C12 C13 Cl4 -9.9(4) . . . . ?
C12 C13 C14 C15 0.9(5) . . . . ?
Cl4 C13 C14 C15 -176.6(3) . . . . ?
C12 C13 C14 Cl5 -179.8(2) . . . . ?
Cl4 C13 C14 Cl5 2.7(4) . . . . ?
C13 C14 C15 C16 -2.0(5) . . . . ?
Cl5 C14 C15 C16 178.7(2) . . . . ?
C13 C14 C15 Cl6 178.3(2) . . . . ?
Cl5 C14 C15 Cl6 -0.9(4) . . . . ?
C14 C15 C16 C17 1.2(5) . . . . ?
Cl6 C15 C16 C17 -179.2(2) . . . . ?
C14 C15 C16 Cl7 -178.2(2) . . . . ?
Cl6 C15 C16 Cl7 1.5(4) . . . . ?
C15 C16 C17 C12 0.8(5) . . . . ?
Cl7 C16 C17 C12 -179.9(2) . . . . ?
C15 C16 C17 Cl8 178.8(2) . . . . ?
Cl7 C16 C17 Cl8 -1.9(4) . . . . ?
C13 C12 C17 C16 -1.8(5) . . . . ?
P1 C12 C17 C16 -174.9(2) . . . . ?
C13 C12 C17 Cl8 -179.8(2) . . . . ?
P1 C12 C17 Cl8 7.1(3) . . . . ?
C6 C5 C18 C19 4.4(5) . . . . ?
P1 C5 C18 C19 -169.4(3) . . . . ?
C6 C5 C18 Cl9 -174.0(2) . . . . ?
P1 C5 C18 Cl9 12.2(3) . . . . ?
C5 C18 C19 C8 -0.9(5) . . . . ?
Cl9 C18 C19 C8 177.5(2) . . . . ?
C5 C18 C19 Cl10 178.5(2) . . . . ?
Cl9 C18 C19 Cl10 -3.1(4) . . . . ?
C7 C8 C19 C18 -2.9(5) . . . . ?
Cl1 C8 C19 C18 178.0(3) . . . . ?
C7 C8 C19 Cl10 177.7(2) . . . . ?
Cl1 C8 C19 Cl10 -1.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.456
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.117
####################################################################### 
# 
# 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_sp019_0m_sqd
_database_code_depnum_ccdc_archive 'CCDC 1471989'
_audit_update_record             
;
2016-04-04 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C42 H5 B Cl10 F21 O0 P'
_chemical_formula_weight         1304.74

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 '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'
Cl Cl 0.1484 0.1585 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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                   11.8072(4)
_cell_length_b                   20.1065(8)
_cell_length_c                   21.8370(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.528(2)
_cell_angle_gamma                90.00
_cell_volume                     5096.9(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4852
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      22.06

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.700
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2544
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8747
_exptl_absorpt_correction_T_max  0.9344
_exptl_absorpt_process_details   ?

_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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46119
_diffrn_reflns_av_R_equivalents  0.1077
_diffrn_reflns_av_sigmaI/netI    0.1674
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.03
_diffrn_reflns_theta_max         27.50
_reflns_number_total             11706
_reflns_number_gt                5178
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0632P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11706
_refine_ls_number_parameters     676
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1131
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1043
_refine_ls_wR_factor_gt          0.0872
_refine_ls_goodness_of_fit_ref   0.603
_refine_ls_restrained_S_all      0.603
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

# SQUEEZE RESULTS (Version = 150216)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.016 0.163 0.640 216 82 ' '
2 0.016 0.837 0.360 215 82 ' '
3 0.484 0.337 0.140 216 82 ' '
4 0.516 0.663 0.860 216 82 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          ?





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
Cl1 Cl 0.34036(8) 0.04551(5) 0.41762(5) 0.0408(3) Uani 1 1 d . . .
Cl2 Cl -0.02175(10) 0.47837(5) 0.20655(5) 0.0549(3) Uani 1 1 d . . .
Cl3 Cl 0.08568(7) 0.16303(5) 0.21844(4) 0.0268(2) Uani 1 1 d . . .
Cl4 Cl 0.00936(9) 0.28870(5) 0.37985(4) 0.0392(3) Uani 1 1 d . . .
Cl5 Cl -0.16037(8) 0.23322(5) 0.13696(4) 0.0350(2) Uani 1 1 d . . .
Cl6 Cl -0.13017(9) 0.37921(5) 0.10477(4) 0.0408(3) Uani 1 1 d . . .
Cl7 Cl 0.06470(9) 0.43014(5) 0.34218(5) 0.0446(3) Uani 1 1 d . . .
Cl8 Cl -0.09554(8) 0.11242(6) 0.42367(4) 0.0435(3) Uani 1 1 d . . .
Cl9 Cl 0.13307(8) 0.04967(5) 0.48589(4) 0.0390(2) Uani 1 1 d . . .
Cl10 Cl 0.31790(8) 0.10385(5) 0.28362(4) 0.0356(2) Uani 1 1 d . . .
P1 P -0.11740(7) 0.18525(5) 0.28582(4) 0.0222(2) Uani 1 1 d . . .
F1 F 1.37783(17) 0.05292(11) 0.06800(9) 0.0376(5) Uani 1 1 d . . .
F2 F 0.53999(17) 0.16332(11) 0.04126(9) 0.0385(6) Uani 1 1 d . . .
F3 F 1.15853(18) 0.44825(10) -0.05379(10) 0.0404(6) Uani 1 1 d . . .
F4 F 1.11823(18) 0.38553(11) 0.05095(9) 0.0389(6) Uani 1 1 d . . .
F5 F 1.02631(16) 0.26441(10) 0.04392(8) 0.0295(5) Uani 1 1 d . . .
F6 F 1.01934(16) 0.26377(10) -0.17407(8) 0.0287(5) Uani 1 1 d . . .
F7 F 1.10781(17) 0.38470(10) -0.16529(9) 0.0342(5) Uani 1 1 d . . .
F8 F 1.01044(16) 0.04572(10) -0.11992(9) 0.0313(5) Uani 1 1 d . . .
F9 F 0.91099(17) 0.00045(11) -0.22951(9) 0.0388(5) Uani 1 1 d . . .
F10 F 0.78860(16) 0.24388(9) -0.15760(8) 0.0275(5) Uani 1 1 d . . .
F11 F 0.68830(16) 0.19527(10) -0.26758(9) 0.0333(5) Uani 1 1 d . . .
F12 F 0.74864(19) 0.07376(11) -0.30583(9) 0.0464(6) Uani 1 1 d . . .
F13 F 1.00154(17) 0.12259(10) 0.07031(8) 0.0342(5) Uani 1 1 d . . .
F14 F 1.16673(16) 0.15460(10) -0.11024(8) 0.0309(5) Uani 1 1 d . . .
F15 F 1.19509(18) 0.06471(11) 0.12573(9) 0.0402(6) Uani 1 1 d . . .
F16 F 0.80691(15) 0.29754(9) -0.03195(8) 0.0260(5) Uani 1 1 d . . .
F17 F 0.65765(19) 0.05203(11) 0.01729(9) 0.0427(6) Uani 1 1 d . . .
F18 F 0.85040(18) 0.06275(10) -0.02879(9) 0.0348(5) Uani 1 1 d . . .
F19 F 0.61906(16) 0.28517(10) 0.01523(9) 0.0329(5) Uani 1 1 d . . .
F20 F -0.19256(16) 0.20600(10) 0.33325(8) 0.0308(5) Uani 1 1 d . . .
C1 C 1.2792(3) 0.08109(18) 0.03746(17) 0.0289(9) Uani 1 1 d . . .
C2 C 1.1868(3) 0.08710(18) 0.06678(15) 0.0291(9) Uani 1 1 d . . .
C3 C 1.0865(3) 0.11638(18) 0.03627(15) 0.0270(8) Uani 1 1 d . . .
C4 C 1.0714(3) 0.14031(16) -0.02467(14) 0.0204(8) Uani 1 1 d . . .
C5 C 0.8440(3) 0.18036(18) -0.03073(14) 0.0224(8) Uani 1 1 d . . .
C6 C 0.7781(3) 0.23451(17) -0.01922(14) 0.0208(8) Uani 1 1 d . . .
C7 C 0.6783(3) 0.22949(19) 0.00549(15) 0.0255(8) Uani 1 1 d . . .
C8 C 0.6380(3) 0.16864(19) 0.01881(14) 0.0257(8) Uani 1 1 d . . .
C9 C 1.1134(3) 0.38675(18) -0.05714(17) 0.0266(8) Uani 1 1 d . . .
C10 C 1.0918(3) 0.35490(18) -0.00527(16) 0.0244(8) Uani 1 1 d . . .
C11 C 1.0441(3) 0.29271(18) -0.01016(15) 0.0229(8) Uani 1 1 d . . .
C12 C 1.0133(3) 0.25755(16) -0.06573(15) 0.0196(7) Uani 1 1 d . . .
C13 C 1.0397(3) 0.29193(17) -0.11655(15) 0.0202(8) Uani 1 1 d . . .
C14 C 1.0873(3) 0.35418(18) -0.11296(16) 0.0255(8) Uani 1 1 d . . .
C15 C 0.9090(3) 0.14906(16) -0.13261(14) 0.0193(7) Uani 1 1 d . . .
C16 C 0.9331(3) 0.08712(17) -0.15431(15) 0.0220(8) Uani 1 1 d . . .
C17 C 0.8814(3) 0.06153(18) -0.21111(16) 0.0270(8) Uani 1 1 d . . .
C18 C 0.7995(3) 0.09770(19) -0.24952(15) 0.0273(9) Uani 1 1 d . . .
C19 C 0.7703(3) 0.15934(18) -0.23032(16) 0.0254(8) Uani 1 1 d . . .
C20 C 0.8237(3) 0.18286(17) -0.17366(15) 0.0214(8) Uani 1 1 d . . .
C21 C 1.2708(3) 0.10333(18) -0.02220(16) 0.0248(8) Uani 1 1 d . . .
C23 C 1.1693(3) 0.13231(18) -0.05096(15) 0.0253(8) Uani 1 1 d . . .
C24 C 0.6972(3) 0.11249(19) 0.00655(15) 0.0286(9) Uani 1 1 d . . .
C25 C 0.7979(3) 0.11972(18) -0.01733(15) 0.0252(8) Uani 1 1 d . . .
C26 C 0.2146(3) 0.08192(17) 0.38291(15) 0.0252(8) Uani 1 1 d . . .
C27 C 0.2056(3) 0.10852(18) 0.32275(16) 0.0241(8) Uani 1 1 d . . .
C28 C 0.1024(3) 0.13728(17) 0.29470(14) 0.0218(8) Uani 1 1 d . . .
C29 C 0.0090(3) 0.14244(17) 0.32574(15) 0.0212(8) Uani 1 1 d . . .
C30 C -0.0826(3) 0.26565(18) 0.25820(14) 0.0223(8) Uani 1 1 d . . .
C31 C -0.1087(3) 0.28721(18) 0.19630(15) 0.0237(8) Uani 1 1 d . . .
C32 C -0.0903(3) 0.35297(19) 0.18081(16) 0.0275(9) Uani 1 1 d . . .
C33 C -0.0412(3) 0.39752(18) 0.22600(17) 0.0287(9) Uani 1 1 d . . .
C34 C -0.2062(3) 0.13152(18) 0.23450(15) 0.0239(8) Uani 1 1 d . . .
C35 C -0.1630(3) 0.07276(19) 0.21483(17) 0.0319(9) Uani 1 1 d . . .
H35 H -0.0846 0.0611 0.2289 0.038 Uiso 1 1 calc R . .
C36 C -0.2345(3) 0.0311(2) 0.17456(18) 0.0395(10) Uani 1 1 d . . .
H36 H -0.2055 -0.0093 0.1608 0.047 Uiso 1 1 calc R . .
C37 C -0.3483(3) 0.0485(2) 0.15455(16) 0.0365(10) Uani 1 1 d . . .
H37 H -0.3970 0.0207 0.1260 0.044 Uiso 1 1 calc R . .
C38 C -0.3917(3) 0.1058(2) 0.17555(16) 0.0354(10) Uani 1 1 d . . .
H38 H -0.4709 0.1162 0.1624 0.042 Uiso 1 1 calc R . .
C39 C -0.3221(3) 0.1485(2) 0.21544(16) 0.0310(9) Uani 1 1 d . . .
H39 H -0.3522 0.1883 0.2295 0.037 Uiso 1 1 calc R . .
C40 C -0.0308(3) 0.31230(18) 0.30330(15) 0.0244(8) Uani 1 1 d . . .
C41 C -0.0071(3) 0.37674(18) 0.28698(16) 0.0282(9) Uani 1 1 d . . .
C42 C 0.0193(3) 0.11407(18) 0.38531(15) 0.0242(8) Uani 1 1 d . . .
C43 C 0.1206(3) 0.08432(17) 0.41341(15) 0.0262(8) Uani 1 1 d . . .
B1 B 0.9596(3) 0.1815(2) -0.06362(17) 0.0215(9) Uani 1 1 d . . .
F0AA F 1.35961(16) 0.09608(11) -0.05264(9) 0.0357(5) 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
Cl1 C26 1.704(3) . ?
Cl2 C33 1.706(4) . ?
Cl3 C28 1.721(3) . ?
Cl4 C40 1.719(3) . ?
Cl5 C31 1.715(3) . ?
Cl6 C32 1.724(3) . ?
Cl7 C41 1.718(4) . ?
Cl8 C42 1.720(3) . ?
Cl9 C43 1.711(3) . ?
Cl10 C27 1.707(3) . ?
P1 F20 1.5395(19) . ?
P1 C34 1.759(3) . ?
P1 C30 1.799(4) . ?
P1 C29 1.803(3) . ?
F1 C1 1.356(4) . ?
F2 C8 1.341(4) . ?
F3 C9 1.343(4) . ?
F4 C10 1.358(4) . ?
F5 C11 1.361(4) . ?
F6 C13 1.359(4) . ?
F7 C14 1.357(4) . ?
F8 C16 1.357(4) . ?
F9 C17 1.357(4) . ?
F10 C20 1.361(4) . ?
F11 C19 1.354(4) . ?
F12 C18 1.354(4) . ?
F13 C3 1.359(4) . ?
F14 C23 1.365(4) . ?
F15 C2 1.350(4) . ?
F16 C6 1.354(4) . ?
F17 C24 1.338(4) . ?
F18 C25 1.348(4) . ?
F19 C7 1.357(4) . ?
C1 C2 1.367(5) . ?
C1 C21 1.364(5) . ?
C2 C3 1.380(5) . ?
C3 C4 1.395(4) . ?
C4 C23 1.392(4) . ?
C4 B1 1.656(5) . ?
C5 C25 1.388(5) . ?
C5 C6 1.388(5) . ?
C5 B1 1.654(5) . ?
C6 C7 1.386(4) . ?
C7 C8 1.363(5) . ?
C8 C24 1.379(5) . ?
C9 C14 1.368(5) . ?
C9 C10 1.365(5) . ?
C10 C11 1.368(5) . ?
C11 C12 1.394(4) . ?
C12 C13 1.391(4) . ?
C12 B1 1.659(5) . ?
C13 C14 1.368(5) . ?
C15 C16 1.381(4) . ?
C15 C20 1.396(4) . ?
C15 B1 1.650(5) . ?
C16 C17 1.378(5) . ?
C17 C18 1.368(5) . ?
C18 C19 1.373(5) . ?
C19 C20 1.367(5) . ?
C21 F0AA 1.348(4) . ?
C21 C23 1.376(5) . ?
C24 C25 1.391(5) . ?
C26 C43 1.396(5) . ?
C26 C27 1.404(5) . ?
C27 C28 1.386(5) . ?
C28 C29 1.400(4) . ?
C29 C42 1.405(4) . ?
C30 C40 1.415(5) . ?
C30 C31 1.399(4) . ?
C31 C32 1.392(5) . ?
C32 C33 1.379(5) . ?
C33 C41 1.383(5) . ?
C34 C35 1.386(5) . ?
C34 C39 1.397(5) . ?
C35 C36 1.385(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.380(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.373(5) . ?
C37 H37 0.9500 . ?
C38 C39 1.382(5) . ?
C38 H38 0.9500 . ?
C39 H39 0.9500 . ?
C40 C41 1.386(5) . ?
C42 C43 1.376(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
F20 P1 C34 104.19(13) . . ?
F20 P1 C30 100.22(14) . . ?
C34 P1 C30 118.97(16) . . ?
F20 P1 C29 109.39(13) . . ?
C34 P1 C29 111.05(16) . . ?
C30 P1 C29 111.79(15) . . ?
F1 C1 C2 119.6(3) . . ?
F1 C1 C21 120.9(3) . . ?
C2 C1 C21 119.6(3) . . ?
F15 C2 C1 119.5(3) . . ?
F15 C2 C3 120.6(3) . . ?
C1 C2 C3 120.0(3) . . ?
F13 C3 C2 115.4(3) . . ?
F13 C3 C4 120.8(3) . . ?
C2 C3 C4 123.8(3) . . ?
C23 C4 C3 112.5(3) . . ?
C23 C4 B1 119.4(3) . . ?
C3 C4 B1 127.8(3) . . ?
C25 C5 C6 113.4(3) . . ?
C25 C5 B1 119.4(3) . . ?
C6 C5 B1 127.0(3) . . ?
F16 C6 C7 114.3(3) . . ?
F16 C6 C5 121.8(3) . . ?
C7 C6 C5 123.9(3) . . ?
F19 C7 C8 119.8(3) . . ?
F19 C7 C6 120.0(3) . . ?
C8 C7 C6 120.2(3) . . ?
F2 C8 C7 120.5(3) . . ?
F2 C8 C24 120.5(3) . . ?
C7 C8 C24 119.0(3) . . ?
F3 C9 C14 120.8(3) . . ?
F3 C9 C10 121.3(3) . . ?
C14 C9 C10 118.0(3) . . ?
F4 C10 C11 120.6(3) . . ?
F4 C10 C9 119.4(3) . . ?
C11 C10 C9 120.1(3) . . ?
F5 C11 C10 116.2(3) . . ?
F5 C11 C12 119.1(3) . . ?
C10 C11 C12 124.7(3) . . ?
C13 C12 C11 112.4(3) . . ?
C13 C12 B1 128.5(3) . . ?
C11 C12 B1 118.9(3) . . ?
F6 C13 C14 115.8(3) . . ?
F6 C13 C12 120.2(3) . . ?
C14 C13 C12 124.0(3) . . ?
F7 C14 C9 119.2(3) . . ?
F7 C14 C13 120.0(3) . . ?
C9 C14 C13 120.8(3) . . ?
C16 C15 C20 112.9(3) . . ?
C16 C15 B1 127.4(3) . . ?
C20 C15 B1 119.5(3) . . ?
F8 C16 C17 114.3(3) . . ?
F8 C16 C15 121.6(3) . . ?
C17 C16 C15 124.1(3) . . ?
F9 C17 C18 119.4(3) . . ?
F9 C17 C16 120.6(3) . . ?
C18 C17 C16 120.0(3) . . ?
F12 C18 C17 121.0(3) . . ?
F12 C18 C19 120.2(3) . . ?
C17 C18 C19 118.8(3) . . ?
F11 C19 C20 121.4(3) . . ?
F11 C19 C18 119.4(3) . . ?
C20 C19 C18 119.2(3) . . ?
F10 C20 C19 115.6(3) . . ?
F10 C20 C15 119.4(3) . . ?
C19 C20 C15 124.9(3) . . ?
F0AA C21 C1 120.5(3) . . ?
F0AA C21 C23 120.7(3) . . ?
C1 C21 C23 118.7(3) . . ?
F14 C23 C21 116.0(3) . . ?
F14 C23 C4 118.5(3) . . ?
C21 C23 C4 125.5(3) . . ?
F17 C24 C8 120.3(3) . . ?
F17 C24 C25 120.7(3) . . ?
C8 C24 C25 119.0(3) . . ?
F18 C25 C24 115.8(3) . . ?
F18 C25 C5 119.7(3) . . ?
C24 C25 C5 124.5(3) . . ?
C43 C26 C27 120.2(3) . . ?
C43 C26 Cl1 120.5(3) . . ?
C27 C26 Cl1 119.4(3) . . ?
C28 C27 C26 118.8(3) . . ?
C28 C27 Cl10 120.2(3) . . ?
C26 C27 Cl10 121.0(3) . . ?
C27 C28 C29 121.6(3) . . ?
C27 C28 Cl3 119.3(2) . . ?
C29 C28 Cl3 119.0(3) . . ?
C28 C29 C42 118.4(3) . . ?
C28 C29 P1 117.2(2) . . ?
C42 C29 P1 124.4(2) . . ?
C40 C30 C31 117.3(3) . . ?
C40 C30 P1 117.3(2) . . ?
C31 C30 P1 125.4(3) . . ?
C32 C31 C30 120.8(3) . . ?
C32 C31 Cl5 117.9(3) . . ?
C30 C31 Cl5 121.3(3) . . ?
C33 C32 C31 120.5(3) . . ?
C33 C32 Cl6 119.7(3) . . ?
C31 C32 Cl6 119.8(3) . . ?
C41 C33 C32 120.2(3) . . ?
C41 C33 Cl2 119.9(3) . . ?
C32 C33 Cl2 119.9(3) . . ?
C35 C34 C39 120.8(3) . . ?
C35 C34 P1 120.7(3) . . ?
C39 C34 P1 118.5(3) . . ?
C36 C35 C34 119.7(3) . . ?
C36 C35 H35 120.1 . . ?
C34 C35 H35 120.1 . . ?
C37 C36 C35 119.5(4) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C36 C37 C38 120.6(4) . . ?
C36 C37 H37 119.7 . . ?
C38 C37 H37 119.7 . . ?
C37 C38 C39 121.1(4) . . ?
C37 C38 H38 119.5 . . ?
C39 C38 H38 119.5 . . ?
C38 C39 C34 118.2(4) . . ?
C38 C39 H39 120.9 . . ?
C34 C39 H39 120.9 . . ?
C41 C40 C30 121.5(3) . . ?
C41 C40 Cl4 118.4(3) . . ?
C30 C40 Cl4 120.1(3) . . ?
C33 C41 C40 119.5(3) . . ?
C33 C41 Cl7 120.4(3) . . ?
C40 C41 Cl7 120.1(3) . . ?
C43 C42 C29 120.7(3) . . ?
C43 C42 Cl8 118.2(3) . . ?
C29 C42 Cl8 121.0(3) . . ?
C42 C43 C26 120.2(3) . . ?
C42 C43 Cl9 120.7(3) . . ?
C26 C43 Cl9 119.1(3) . . ?
C15 B1 C12 114.6(3) . . ?
C15 B1 C4 113.1(3) . . ?
C12 B1 C4 101.7(3) . . ?
C15 B1 C5 101.6(3) . . ?
C12 B1 C5 112.0(3) . . ?
C4 B1 C5 114.4(3) . . ?

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
F1 C1 C2 F15 -0.2(5) . . . . ?
C21 C1 C2 F15 179.6(3) . . . . ?
F1 C1 C2 C3 179.3(3) . . . . ?
C21 C1 C2 C3 -0.9(6) . . . . ?
F15 C2 C3 F13 2.2(5) . . . . ?
C1 C2 C3 F13 -177.3(3) . . . . ?
F15 C2 C3 C4 -179.6(3) . . . . ?
C1 C2 C3 C4 0.9(6) . . . . ?
F13 C3 C4 C23 177.1(3) . . . . ?
C2 C3 C4 C23 -0.9(5) . . . . ?
F13 C3 C4 B1 3.5(5) . . . . ?
C2 C3 C4 B1 -174.6(3) . . . . ?
C25 C5 C6 F16 -177.2(3) . . . . ?
B1 C5 C6 F16 -3.3(5) . . . . ?
C25 C5 C6 C7 2.4(5) . . . . ?
B1 C5 C6 C7 176.3(3) . . . . ?
F16 C6 C7 F19 -0.3(4) . . . . ?
C5 C6 C7 F19 -180.0(3) . . . . ?
F16 C6 C7 C8 178.2(3) . . . . ?
C5 C6 C7 C8 -1.4(5) . . . . ?
F19 C7 C8 F2 0.2(5) . . . . ?
C6 C7 C8 F2 -178.3(3) . . . . ?
F19 C7 C8 C24 177.7(3) . . . . ?
C6 C7 C8 C24 -0.8(5) . . . . ?
F3 C9 C10 F4 -1.1(5) . . . . ?
C14 C9 C10 F4 179.1(3) . . . . ?
F3 C9 C10 C11 178.9(3) . . . . ?
C14 C9 C10 C11 -0.9(5) . . . . ?
F4 C10 C11 F5 -0.5(5) . . . . ?
C9 C10 C11 F5 179.5(3) . . . . ?
F4 C10 C11 C12 179.5(3) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
F5 C11 C12 C13 -178.2(3) . . . . ?
C10 C11 C12 C13 1.8(5) . . . . ?
F5 C11 C12 B1 -1.7(4) . . . . ?
C10 C11 C12 B1 178.3(3) . . . . ?
C11 C12 C13 F6 177.6(3) . . . . ?
B1 C12 C13 F6 1.6(5) . . . . ?
C11 C12 C13 C14 -1.9(5) . . . . ?
B1 C12 C13 C14 -178.0(3) . . . . ?
F3 C9 C14 F7 0.2(5) . . . . ?
C10 C9 C14 F7 180.0(3) . . . . ?
F3 C9 C14 C13 -179.0(3) . . . . ?
C10 C9 C14 C13 0.8(5) . . . . ?
F6 C13 C14 F7 2.0(4) . . . . ?
C12 C13 C14 F7 -178.5(3) . . . . ?
F6 C13 C14 C9 -178.8(3) . . . . ?
C12 C13 C14 C9 0.7(5) . . . . ?
C20 C15 C16 F8 -177.5(3) . . . . ?
B1 C15 C16 F8 -3.8(5) . . . . ?
C20 C15 C16 C17 1.7(5) . . . . ?
B1 C15 C16 C17 175.4(3) . . . . ?
F8 C16 C17 F9 -1.6(5) . . . . ?
C15 C16 C17 F9 179.1(3) . . . . ?
F8 C16 C17 C18 178.3(3) . . . . ?
C15 C16 C17 C18 -1.0(5) . . . . ?
F9 C17 C18 F12 -0.8(5) . . . . ?
C16 C17 C18 F12 179.3(3) . . . . ?
F9 C17 C18 C19 179.9(3) . . . . ?
C16 C17 C18 C19 -0.1(5) . . . . ?
F12 C18 C19 F11 1.5(5) . . . . ?
C17 C18 C19 F11 -179.2(3) . . . . ?
F12 C18 C19 C20 -179.2(3) . . . . ?
C17 C18 C19 C20 0.2(5) . . . . ?
F11 C19 C20 F10 0.4(5) . . . . ?
C18 C19 C20 F10 -179.0(3) . . . . ?
F11 C19 C20 C15 -179.9(3) . . . . ?
C18 C19 C20 C15 0.7(5) . . . . ?
C16 C15 C20 F10 178.1(3) . . . . ?
B1 C15 C20 F10 3.8(4) . . . . ?
C16 C15 C20 C19 -1.6(5) . . . . ?
B1 C15 C20 C19 -175.9(3) . . . . ?
F1 C1 C21 F0AA 1.8(5) . . . . ?
C2 C1 C21 F0AA -178.0(3) . . . . ?
F1 C1 C21 C23 -179.2(3) . . . . ?
C2 C1 C21 C23 1.0(5) . . . . ?
F0AA C21 C23 F14 -2.1(5) . . . . ?
C1 C21 C23 F14 178.9(3) . . . . ?
F0AA C21 C23 C4 177.8(3) . . . . ?
C1 C21 C23 C4 -1.2(6) . . . . ?
C3 C4 C23 F14 -179.0(3) . . . . ?
B1 C4 C23 F14 -4.8(5) . . . . ?
C3 C4 C23 C21 1.1(5) . . . . ?
B1 C4 C23 C21 175.3(3) . . . . ?
F2 C8 C24 F17 -0.4(5) . . . . ?
C7 C8 C24 F17 -177.9(3) . . . . ?
F2 C8 C24 C25 179.3(3) . . . . ?
C7 C8 C24 C25 1.8(5) . . . . ?
F17 C24 C25 F18 0.4(5) . . . . ?
C8 C24 C25 F18 -179.3(3) . . . . ?
F17 C24 C25 C5 179.0(3) . . . . ?
C8 C24 C25 C5 -0.7(5) . . . . ?
C6 C5 C25 F18 177.2(3) . . . . ?
B1 C5 C25 F18 2.8(5) . . . . ?
C6 C5 C25 C24 -1.3(5) . . . . ?
B1 C5 C25 C24 -175.7(3) . . . . ?
C43 C26 C27 C28 0.3(5) . . . . ?
Cl1 C26 C27 C28 179.2(3) . . . . ?
C43 C26 C27 Cl10 -178.0(3) . . . . ?
Cl1 C26 C27 Cl10 0.9(4) . . . . ?
C26 C27 C28 C29 2.3(5) . . . . ?
Cl10 C27 C28 C29 -179.4(3) . . . . ?
C26 C27 C28 Cl3 -174.0(3) . . . . ?
Cl10 C27 C28 Cl3 4.3(4) . . . . ?
C27 C28 C29 C42 -3.8(5) . . . . ?
Cl3 C28 C29 C42 172.5(3) . . . . ?
C27 C28 C29 P1 176.5(3) . . . . ?
Cl3 C28 C29 P1 -7.2(4) . . . . ?
F20 P1 C29 C28 -161.6(2) . . . . ?
C34 P1 C29 C28 83.9(3) . . . . ?
C30 P1 C29 C28 -51.5(3) . . . . ?
F20 P1 C29 C42 18.6(3) . . . . ?
C34 P1 C29 C42 -95.8(3) . . . . ?
C30 P1 C29 C42 128.7(3) . . . . ?
F20 P1 C30 C40 55.1(3) . . . . ?
C34 P1 C30 C40 167.7(2) . . . . ?
C29 P1 C30 C40 -60.7(3) . . . . ?
F20 P1 C30 C31 -120.8(3) . . . . ?
C34 P1 C30 C31 -8.2(4) . . . . ?
C29 P1 C30 C31 123.4(3) . . . . ?
C40 C30 C31 C32 -3.6(5) . . . . ?
P1 C30 C31 C32 172.3(3) . . . . ?
C40 C30 C31 Cl5 174.5(2) . . . . ?
P1 C30 C31 Cl5 -9.6(4) . . . . ?
C30 C31 C32 C33 2.8(5) . . . . ?
Cl5 C31 C32 C33 -175.4(3) . . . . ?
C30 C31 C32 Cl6 -176.6(2) . . . . ?
Cl5 C31 C32 Cl6 5.2(4) . . . . ?
C31 C32 C33 C41 1.6(5) . . . . ?
Cl6 C32 C33 C41 -178.9(3) . . . . ?
C31 C32 C33 Cl2 -178.7(3) . . . . ?
Cl6 C32 C33 Cl2 0.7(4) . . . . ?
F20 P1 C34 C35 -136.5(3) . . . . ?
C30 P1 C34 C35 113.1(3) . . . . ?
C29 P1 C34 C35 -18.8(3) . . . . ?
F20 P1 C34 C39 41.7(3) . . . . ?
C30 P1 C34 C39 -68.7(3) . . . . ?
C29 P1 C34 C39 159.4(3) . . . . ?
C39 C34 C35 C36 1.6(5) . . . . ?
P1 C34 C35 C36 179.8(3) . . . . ?
C34 C35 C36 C37 -0.1(6) . . . . ?
C35 C36 C37 C38 -1.8(6) . . . . ?
C36 C37 C38 C39 2.2(6) . . . . ?
C37 C38 C39 C34 -0.7(5) . . . . ?
C35 C34 C39 C38 -1.2(5) . . . . ?
P1 C34 C39 C38 -179.4(3) . . . . ?
C31 C30 C40 C41 0.1(5) . . . . ?
P1 C30 C40 C41 -176.1(3) . . . . ?
C31 C30 C40 Cl4 -177.3(2) . . . . ?
P1 C30 C40 Cl4 6.5(4) . . . . ?
C32 C33 C41 C40 -5.1(5) . . . . ?
Cl2 C33 C41 C40 175.3(3) . . . . ?
C32 C33 C41 Cl7 174.6(3) . . . . ?
Cl2 C33 C41 Cl7 -5.0(4) . . . . ?
C30 C40 C41 C33 4.2(5) . . . . ?
Cl4 C40 C41 C33 -178.4(3) . . . . ?
C30 C40 C41 Cl7 -175.5(3) . . . . ?
Cl4 C40 C41 Cl7 1.9(4) . . . . ?
C28 C29 C42 C43 2.6(5) . . . . ?
P1 C29 C42 C43 -177.6(3) . . . . ?
C28 C29 C42 Cl8 -174.6(3) . . . . ?
P1 C29 C42 Cl8 5.1(4) . . . . ?
C29 C42 C43 C26 0.0(5) . . . . ?
Cl8 C42 C43 C26 177.3(3) . . . . ?
C29 C42 C43 Cl9 -179.9(3) . . . . ?
Cl8 C42 C43 Cl9 -2.6(4) . . . . ?
C27 C26 C43 C42 -1.5(5) . . . . ?
Cl1 C26 C43 C42 179.7(3) . . . . ?
C27 C26 C43 Cl9 178.4(3) . . . . ?
Cl1 C26 C43 Cl9 -0.5(4) . . . . ?
C16 C15 B1 C12 130.1(3) . . . . ?
C20 C15 B1 C12 -56.6(4) . . . . ?
C16 C15 B1 C4 14.2(5) . . . . ?
C20 C15 B1 C4 -172.5(3) . . . . ?
C16 C15 B1 C5 -108.9(4) . . . . ?
C20 C15 B1 C5 64.4(4) . . . . ?
C13 C12 B1 C15 -12.6(5) . . . . ?
C11 C12 B1 C15 171.6(3) . . . . ?
C13 C12 B1 C4 109.7(4) . . . . ?
C11 C12 B1 C4 -66.1(3) . . . . ?
C13 C12 B1 C5 -127.7(3) . . . . ?
C11 C12 B1 C5 56.5(4) . . . . ?
C23 C4 B1 C15 58.0(4) . . . . ?
C3 C4 B1 C15 -128.8(3) . . . . ?
C23 C4 B1 C12 -65.4(4) . . . . ?
C3 C4 B1 C12 107.9(4) . . . . ?
C23 C4 B1 C5 173.6(3) . . . . ?
C3 C4 B1 C5 -13.1(5) . . . . ?
C25 C5 B1 C15 66.2(4) . . . . ?
C6 C5 B1 C15 -107.3(4) . . . . ?
C25 C5 B1 C12 -171.0(3) . . . . ?
C6 C5 B1 C12 15.4(5) . . . . ?
C25 C5 B1 C4 -56.0(4) . . . . ?
C6 C5 B1 C4 130.5(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.419
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.100
####################################################################### 
# 
# 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_sad
_database_code_depnum_ccdc_archive 'CCDC 1471990'
_audit_update_record             
;
2016-04-04 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C6 Cl5'
_chemical_formula_weight         249.31

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   13.3969(9)
_cell_length_b                   10.5584(8)
_cell_length_c                   11.6957(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1654.4(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8430
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.39

_exptl_crystal_description       triangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.40
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.002
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    1.673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4885
_exptl_absorpt_correction_T_max  0.5543
_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'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25237
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_sigmaI/netI    0.0196
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         27.54
_reflns_number_total             1900
_reflns_number_gt                1627
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0235P)²+1.4917P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   none
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         1900
_refine_ls_number_parameters     100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0244
_refine_ls_wR_factor_ref         0.0600
_refine_ls_wR_factor_gt          0.0561
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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
Cl1 Cl 0.11180(3) 0.36525(6) 0.31980(5) 0.04425(15) Uani 1 1 d . . .
Cl2 Cl 0.20199(4) 0.56191(5) 0.15060(5) 0.04029(14) Uani 1 1 d . . .
Cl3 Cl 0.25143(4) 0.18019(5) 0.45119(4) 0.03670(13) Uani 1 1 d . . .
Cl4 Cl 0.48140(3) 0.19310(4) 0.41433(4) 0.02921(12) Uani 1 1 d . . .
Cl5 Cl 0.43194(4) 0.57257(5) 0.11249(4) 0.03570(13) Uani 1 1 d . . .
C1 C 0.23870(12) 0.37159(18) 0.29913(16) 0.0261(4) Uani 1 1 d . . .
C2 C 0.27867(13) 0.45870(18) 0.22285(15) 0.0261(4) Uani 1 1 d . . .
C3 C 0.38175(13) 0.46238(17) 0.20492(15) 0.0236(4) Uani 1 1 d . . .
C4 C 0.44491(11) 0.37900(16) 0.26163(14) 0.0195(3) Uani 1 1 d . . .
C5 C 0.30074(12) 0.28947(17) 0.35819(15) 0.0236(4) Uani 1 1 d . . .
C6 C 0.40380(12) 0.29416(16) 0.33948(14) 0.0204(3) 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
Cl1 C1 1.7186(17) . ?
Cl2 C2 1.7196(18) . ?
Cl3 C5 1.7177(18) . ?
Cl4 C6 1.7280(17) . ?
Cl5 C3 1.7246(18) . ?
C1 C5 1.385(3) . ?
C1 C2 1.389(3) . ?
C2 C3 1.397(2) . ?
C3 C4 1.390(2) . ?
C4 C6 1.391(2) . ?
C4 C4 1.501(3) 3_655 ?
C5 C6 1.399(2) . ?

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
C5 C1 C2 120.23(15) . . ?
C5 C1 Cl1 119.93(14) . . ?
C2 C1 Cl1 119.84(14) . . ?
C3 C2 C1 119.72(16) . . ?
C3 C2 Cl2 119.94(15) . . ?
C1 C2 Cl2 120.34(14) . . ?
C2 C3 C4 120.84(16) . . ?
C2 C3 Cl5 119.88(14) . . ?
C4 C3 Cl5 119.28(13) . . ?
C6 C4 C3 118.64(15) . . ?
C6 C4 C4 120.53(14) . 3_655 ?
C3 C4 C4 120.82(14) . 3_655 ?
C1 C5 C6 119.47(16) . . ?
C1 C5 Cl3 120.35(13) . . ?
C6 C5 Cl3 120.16(14) . . ?
C4 C6 C5 121.07(15) . . ?
C4 C6 Cl4 119.41(12) . . ?
C5 C6 Cl4 119.52(13) . . ?

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
C5 C1 C2 C3 0.7(3) . . . . ?
Cl1 C1 C2 C3 -179.04(14) . . . . ?
C5 C1 C2 Cl2 -179.28(14) . . . . ?
Cl1 C1 C2 Cl2 1.0(2) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
Cl2 C2 C3 C4 -179.38(13) . . . . ?
C1 C2 C3 Cl5 -178.67(14) . . . . ?
Cl2 C2 C3 Cl5 1.3(2) . . . . ?
C2 C3 C4 C6 -2.0(3) . . . . ?
Cl5 C3 C4 C6 177.37(13) . . . . ?
C2 C3 C4 C4 177.20(16) . . . 3_655 ?
Cl5 C3 C4 C4 -3.5(2) . . . 3_655 ?
C2 C1 C5 C6 -0.7(3) . . . . ?
Cl1 C1 C5 C6 179.06(13) . . . . ?
C2 C1 C5 Cl3 -179.13(14) . . . . ?
Cl1 C1 C5 Cl3 0.6(2) . . . . ?
C3 C4 C6 C5 2.0(2) . . . . ?
C4 C4 C6 C5 -177.18(16) 3_655 . . . ?
C3 C4 C6 Cl4 -177.94(13) . . . . ?
C4 C4 C6 Cl4 2.9(2) 3_655 . . . ?
C1 C5 C6 C4 -0.7(3) . . . . ?
Cl3 C5 C6 C4 177.79(13) . . . . ?
C1 C5 C6 Cl4 179.23(13) . . . . ?
Cl3 C5 C6 Cl4 -2.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.54
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.058
####################################################################### 
# 
# 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_SP018_0m
_database_code_depnum_ccdc_archive 'CCDC 1471991'
_audit_update_record             
;
2016-04-04 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;
_audit_creation_date             2016-03-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C18 H10 Cl5 P'
_chemical_formula_sum            'C18 H10 Cl5 P'
_chemical_formula_weight         434.52
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.10434 0.09671 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   10.8832(6)
_cell_length_b                   11.0570(5)
_cell_length_c                   29.4458(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3543.4(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7546
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.75
_cell_measurement_theta_min      2.33
_exptl_absorpt_coefficient_mu    0.906
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0777 before and 0.0689 after correction.
The Ratio of minimum to maximum transmission is 0.9116.
The λ/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.6289
_exptl_crystal_description       rectangular
_exptl_crystal_F_000             1751.1942
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_diffrn_reflns_av_R_equivalents  0.1077
_diffrn_reflns_av_unetI/netI     0.0647
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_number            56334
_diffrn_reflns_theta_full        27.5326
_diffrn_reflns_theta_max         27.53
_diffrn_reflns_theta_min         2.33
_diffrn_ambient_temperature      149.95
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.9971
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              0
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              38
_reflns_limit_l_min              0
_reflns_number_gt                2778
_reflns_number_total             4072
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.5089
_refine_diff_density_min         -0.6033
_refine_diff_density_rms         0.1362
_refine_ls_d_res_high            0.7688
_refine_ls_d_res_low             8.7517
_refine_ls_goodness_of_fit_ref   0.8411
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     216
_refine_ls_number_reflns         4072
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      0.8411
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0300P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0574
_refine_ls_wR_factor_ref         0.0630
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C9(H9), C10(H10), C11(H11), C13(H13), C14(H14),
 C17(H17), C18(H18)
;
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual =  -1, Ralpha = 0.044
;
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_refinement_flags_posn
P1 P 0.09613(5) 1.04637(4) 0.884732(19) 0.01956(14) Uani 1.000000 .
Cl2 Cl 0.13906(5) 0.97089(5) 0.669858(18) 0.02710(14) Uani 1.000000 .
Cl3 Cl 0.28862(5) 0.82813(4) 0.834398(18) 0.02385(13) Uani 1.000000 .
Cl4 Cl 0.31957(5) 0.82829(4) 0.731611(19) 0.02318(13) Uani 1.000000 .
Cl5 Cl -0.06397(5) 1.13195(4) 0.713462(19) 0.02518(14) Uani 1.000000 .
Cl6 Cl -0.07820(5) 1.15998(4) 0.817207(19) 0.02599(14) Uani 1.000000 .
C1 C 0.4337(2) 0.8952(2) 0.96040(8) 0.0332(6) Uani 1.000000 .
H1 H 0.5049(2) 0.8654(2) 0.97532(8) 0.0398(7) Uiso 1.000000 R
C2 C 0.3243(2) 0.8343(2) 0.96411(8) 0.0302(6) Uani 1.000000 .
H2 H 0.3196(2) 0.7630(2) 0.98204(8) 0.0362(7) Uiso 1.000000 R
C3 C 0.2198(2) 0.87659(18) 0.94166(7) 0.0230(5) Uani 1.000000 .
H3 H 0.1443(2) 0.83419(18) 0.94448(7) 0.0276(6) Uiso 1.000000 R
C4 C 0.22588(19) 0.98050(17) 0.91520(7) 0.0195(5) Uani 1.000000 .
C5 C 0.11198(18) 1.00294(16) 0.82383(7) 0.0156(5) Uani 1.000000 .
C6 C 0.03344(18) 1.06646(16) 0.79444(7) 0.0179(5) Uani 1.000000 .
C7 C 0.03906(18) 1.05550(16) 0.74760(7) 0.0182(5) Uani 1.000000 .
C8 C 0.12866(19) 0.98232(16) 0.72795(7) 0.0176(5) Uani 1.000000 .
C9 C -0.2395(2) 0.82003(19) 0.92869(7) 0.0291(6) Uani 1.000000 .
H9 H -0.3106(2) 0.77615(19) 0.93758(7) 0.0349(7) Uiso 1.000000 R
C10 C -0.2116(2) 0.9284(2) 0.94973(8) 0.0320(6) Uani 1.000000 .
H10 H -0.2626(2) 0.9584(2) 0.97337(8) 0.0384(7) Uiso 1.000000 R
C11 C -0.1092(2) 0.99276(18) 0.93623(7) 0.0258(5) Uani 1.000000 .
H11 H -0.0903(2) 1.06710(18) 0.95081(7) 0.0309(6) Uiso 1.000000 R
C12 C -0.03343(19) 0.95070(17) 0.90166(7) 0.0188(5) Uani 1.000000 .
C13 C -0.06197(19) 0.84009(17) 0.88129(7) 0.0217(5) Uani 1.000000 .
H13 H -0.01070(19) 0.80887(17) 0.85796(7) 0.0261(6) Uiso 1.000000 R
C14 C -0.16494(19) 0.77562(18) 0.89500(7) 0.0245(5) Uani 1.000000 .
H14 H -0.18385(19) 0.70046(18) 0.88101(7) 0.0294(6) Uiso 1.000000 R
C15 C 0.19624(18) 0.92441(16) 0.80299(7) 0.0164(5) Uani 1.000000 .
C16 C 0.20757(18) 0.91775(16) 0.75563(7) 0.0165(5) Uani 1.000000 .
C17 C 0.4402(2) 1.0011(2) 0.93469(8) 0.0319(6) Uani 1.000000 .
H17 H 0.5156(2) 1.0439(2) 0.93229(8) 0.0383(7) Uiso 1.000000 R
C18 C 0.3369(2) 1.04331(19) 0.91281(7) 0.0254(5) Uani 1.000000 .
H18 H 0.3413(2) 1.11625(19) 0.89584(7) 0.0305(6) Uiso 1.000000 R


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
P1 C4 1.825(2) . ?
P1 C5 1.864(2) . ?
P1 C12 1.832(2) . ?
Cl2 C8 1.719(2) . ?
Cl3 C15 1.7319(19) . ?
Cl4 C16 1.722(2) . ?
Cl5 C7 1.727(2) . ?
Cl6 C6 1.731(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.372(3) . ?
C1 C17 1.396(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 C18 1.395(3) . ?
C5 C6 1.405(3) . ?
C5 C15 1.404(3) . ?
C6 C7 1.386(3) . ?
C7 C8 1.393(3) . ?
C8 C16 1.383(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.383(3) . ?
C9 C14 1.372(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.390(3) . ?
C12 C13 1.397(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.402(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.378(3) . ?
C18 H18 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
C5 P1 C4 107.37(9) . . ?
C12 P1 C4 103.38(9) . . ?
C12 P1 C5 100.61(9) . . ?
C2 C1 H1 120.03(14) . . ?
C17 C1 H1 120.03(14) . . ?
C17 C1 C2 119.9(2) . . ?
H2 C2 C1 119.85(14) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.85(13) . . ?
H3 C3 C2 119.88(13) . . ?
C4 C3 C2 120.2(2) . . ?
C4 C3 H3 119.88(12) . . ?
C3 C4 P1 124.67(16) . . ?
C18 C4 P1 116.52(16) . . ?
C18 C4 C3 118.8(2) . . ?
C6 C5 P1 114.05(14) . . ?
C15 C5 P1 129.80(15) . . ?
C15 C5 C6 115.93(18) . . ?
C5 C6 Cl6 119.16(16) . . ?
C7 C6 Cl6 117.96(15) . . ?
C7 C6 C5 122.86(18) . . ?
C6 C7 Cl5 120.52(16) . . ?
C8 C7 Cl5 119.81(16) . . ?
C8 C7 C6 119.68(18) . . ?
C7 C8 Cl2 120.14(16) . . ?
C16 C8 Cl2 120.52(16) . . ?
C16 C8 C7 119.33(19) . . ?
C10 C9 H9 119.87(14) . . ?
C14 C9 H9 119.87(13) . . ?
C14 C9 C10 120.3(2) . . ?
H10 C10 C9 120.16(14) . . ?
C11 C10 C9 119.7(2) . . ?
C11 C10 H10 120.16(13) . . ?
H11 C11 C10 119.43(13) . . ?
C12 C11 C10 121.1(2) . . ?
C12 C11 H11 119.43(12) . . ?
C11 C12 P1 117.57(15) . . ?
C13 C12 P1 124.05(16) . . ?
C13 C12 C11 118.36(19) . . ?
H13 C13 C12 119.86(12) . . ?
C14 C13 C12 120.3(2) . . ?
C14 C13 H13 119.86(12) . . ?
C13 C14 C9 120.2(2) . . ?
H14 C14 C9 119.88(13) . . ?
H14 C14 C13 119.88(12) . . ?
C5 C15 Cl3 121.73(16) . . ?
C16 C15 Cl3 116.60(15) . . ?
C16 C15 C5 121.65(18) . . ?
C8 C16 Cl4 119.61(16) . . ?
C15 C16 Cl4 120.08(15) . . ?
C15 C16 C8 120.31(18) . . ?
H17 C17 C1 120.13(14) . . ?
C18 C17 C1 119.7(2) . . ?
C18 C17 H17 120.13(13) . . ?
C17 C18 C4 121.0(2) . . ?
H18 C18 C4 119.52(13) . . ?
H18 C18 C17 119.52(13) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_pre_a
_database_code_depnum_ccdc_archive 'CCDC 1471992'
_audit_update_record             
;
2016-04-04 deposited with the CCDC.
2016-04-25 downloaded from the CCDC.
;
_audit_creation_date             2016-03-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_formula_moiety         'C18 H10 Cl5 F2 P'
_chemical_formula_sum            'C18 H10 Cl5 F2 P'
_chemical_formula_weight         472.51
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
P 0.10434 0.09671 6.43450 4.17910 1.78000 1.49080 1.90670 27.15700 0.52600
68.16450 1.11489999294
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.01794 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   11.2850(4)
_cell_length_b                   10.8896(4)
_cell_length_c                   30.4034(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3736.2(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9943
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.48

_exptl_crystal_description       tablet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.6799
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1895.4695
_exptl_absorpt_coefficient_mu    0.882
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6603

_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0502 before and 0.0387 after correction.
The Ratio of minimum to maximum transmission is 0.8856.
The λ/2 correction factor is 0.00150.
;
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            31216
_diffrn_reflns_theta_full        27.4884
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         2.25
_diffrn_ambient_temperature      150.03
_diffrn_measured_fraction_theta_full 0.9991
_diffrn_measured_fraction_theta_max 0.9988
_diffrn_radiation_type           'Mo K\a'
_diffrn_measurement_device_type  'Bruker Apex II CCD detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              0
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              39
_reflns_limit_l_min              0
_reflns_number_gt                3665
_reflns_number_total             4289
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.3881
_refine_diff_density_min         -0.2881
_refine_diff_density_rms         0.0688
_refine_ls_d_res_high            0.7699
_refine_ls_d_res_low             9.0612
_refine_ls_goodness_of_fit_ref   1.0658
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    20
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0255
_refine_ls_restrained_S_all      1.0658
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0274P)²+2.2038P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0603
_refine_ls_wR_factor_ref         0.0654
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C22(H22), C23(H23), C24(H24), C25(H25), C26(H26), C32(H32), C33(H33),
 C34(H34), C35(H35), C36(H36)
;
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_refinement_flags_posn
P1 P 0.38767(4) 0.42020(3) 0.625831(13) 0.01749(9) Uani 1.000000 .
F1 F 0.36788(8) 0.57081(7) 0.62572(3) 0.0218(2) Uani 1.000000 .
F2 F 0.40734(8) 0.26914(8) 0.62981(3) 0.0235(2) Uani 1.000000 .
C11 C 0.29800(13) 0.36029(13) 0.71045(5) 0.0175(3) Uani 1.000000 .
C12 C 0.29509(13) 0.36264(13) 0.75646(5) 0.0182(3) Uani 1.000000 .
C13 C 0.37815(14) 0.43152(14) 0.77952(5) 0.0196(3) Uani 1.000000 .
C14 C 0.46317(14) 0.49878(13) 0.75650(5) 0.0191(3) Uani 1.000000 .
C15 C 0.46439(13) 0.49658(13) 0.71065(5) 0.0177(3) Uani 1.000000 .
Cl1 Cl 0.19181(4) 0.27395(4) 0.684117(12) 0.02431(9) Uani 1.000000 .
Cl2 Cl 0.18975(3) 0.27953(4) 0.784508(13) 0.02370(9) Uani 1.000000 .
Cl4 Cl 0.56517(4) 0.58426(4) 0.785291(14) 0.02746(10) Uani 1.000000 .
Cl3 Cl 0.37601(4) 0.43416(4) 0.835892(13) 0.03129(11) Uani 1.000000 .
Cl5 Cl 0.57331(3) 0.58118(4) 0.684616(13) 0.02498(10) Uani 1.000000 .
C16 C 0.38305(13) 0.42602(13) 0.68669(5) 0.0167(3) Uani 1.000000 .
C21 C 0.25489(14) 0.40086(14) 0.59260(5) 0.0190(3) Uani 1.000000 .
C22 C 0.16164(14) 0.48496(15) 0.59514(5) 0.0235(3) Uani 1.000000 .
H22 H 0.16581(14) 0.55170(15) 0.61520(5) 0.0282(4) Uiso 1.000000 R
C23 C 0.06296(15) 0.47107(17) 0.56837(6) 0.0288(4) Uani 1.000000 .
H23 H -0.00139(15) 0.52693(17) 0.57077(6) 0.0346(4) Uiso 1.000000 R
C24 C 0.05801(16) 0.37606(18) 0.53818(5) 0.0304(4) Uani 1.000000 .
H24 H -0.00905(16) 0.36782(18) 0.51952(5) 0.0365(5) Uiso 1.000000 R
C25 C 0.15032(16) 0.29318(16) 0.53511(5) 0.0285(4) Uani 1.000000 .
H25 H 0.14700(16) 0.22859(16) 0.51414(5) 0.0342(4) Uiso 1.000000 R
C26 C 0.24824(15) 0.30419(15) 0.56271(5) 0.0229(3) Uani 1.000000 .
H26 H 0.31055(15) 0.24570(15) 0.56114(5) 0.0274(4) Uiso 1.000000 R
C31 C 0.52436(14) 0.43428(15) 0.59440(5) 0.0222(3) Uani 1.000000 .
C32 C 0.53662(17) 0.53287(17) 0.56556(6) 0.0335(4) Uani 1.000000 .
H32 H 0.47565(17) 0.59278(17) 0.56365(6) 0.0402(5) Uiso 1.000000 R
C33 C 0.63720(19) 0.5443(2) 0.53960(7) 0.0424(5) Uani 1.000000 .
H33 H 0.64360(19) 0.6105(2) 0.51942(7) 0.0509(6) Uiso 1.000000 R
C34 C 0.72729(17) 0.4605(2) 0.54293(6) 0.0417(5) Uani 1.000000 .
H34 H 0.79656(17) 0.4694(2) 0.52547(6) 0.0500(6) Uiso 1.000000 R
C35 C 0.71721(16) 0.3632(2) 0.57166(6) 0.0401(5) Uani 1.000000 .
H35 H 0.78029(16) 0.3059(2) 0.57426(6) 0.0482(6) Uiso 1.000000 R
C36 C 0.61484(15) 0.34817(17) 0.59702(6) 0.0297(4) Uani 1.000000 .
H36 H 0.60724(15) 0.27927(17) 0.61598(6) 0.0356(5) Uiso 1.000000 R


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
P1 F1 1.6552(9) . ?
P1 F2 1.6643(9) . ?
P1 C16 1.8520(15) . ?
P1 C21 1.8195(16) . ?
P1 C31 1.8209(16) . ?
C11 C12 1.399(2) . ?
C11 Cl1 1.7207(15) . ?
C11 C16 1.398(2) . ?
C12 C13 1.390(2) . ?
C12 Cl2 1.7203(15) . ?
C13 C14 1.395(2) . ?
C13 Cl3 1.7143(16) . ?
C14 C15 1.394(2) . ?
C14 Cl4 1.7197(15) . ?
C15 Cl5 1.7280(15) . ?
C15 C16 1.401(2) . ?
C21 C22 1.397(2) . ?
C21 C26 1.393(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.388(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.384(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.381(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.393(2) . ?
C26 H26 0.9500 . ?
C31 C32 1.393(2) . ?
C31 C36 1.389(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.388(3) . ?
C33 H33 0.9500 . ?
C33 C34 1.370(3) . ?
C34 H34 0.9500 . ?
C34 C35 1.377(3) . ?
C35 H35 0.9500 . ?
C35 C36 1.399(3) . ?
C36 H36 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
F2 P1 F1 175.94(5) . . ?
C16 P1 F1 87.95(6) . . ?
C16 P1 F2 87.99(6) . . ?
C21 P1 F1 90.14(6) . . ?
C21 P1 F2 92.05(6) . . ?
C21 P1 C16 122.38(7) . . ?
C31 P1 F1 91.71(6) . . ?
C31 P1 F2 90.48(6) . . ?
C31 P1 C16 123.04(7) . . ?
C31 P1 C21 114.58(7) . . ?
Cl1 C11 C12 117.30(11) . . ?
C16 C11 C12 121.54(13) . . ?
C16 C11 Cl1 121.15(11) . . ?
C13 C12 C11 119.88(14) . . ?
Cl2 C12 C11 120.14(11) . . ?
Cl2 C12 C13 119.98(12) . . ?
C14 C13 C12 119.59(14) . . ?
Cl3 C13 C12 120.25(12) . . ?
Cl3 C13 C14 120.16(12) . . ?
C15 C14 C13 119.95(14) . . ?
Cl4 C14 C13 119.29(12) . . ?
Cl4 C14 C15 120.77(12) . . ?
Cl5 C15 C14 117.12(11) . . ?
C16 C15 C14 121.52(14) . . ?
C16 C15 Cl5 121.34(12) . . ?
C11 C16 P1 121.19(11) . . ?
C15 C16 P1 121.31(11) . . ?
C15 C16 C11 117.49(14) . . ?
C22 C21 P1 120.91(12) . . ?
C26 C21 P1 119.62(12) . . ?
C26 C21 C22 119.40(15) . . ?
H22 C22 C21 119.98(9) . . ?
C23 C22 C21 120.04(15) . . ?
C23 C22 H22 119.98(10) . . ?
H23 C23 C22 119.91(10) . . ?
C24 C23 C22 120.18(16) . . ?
C24 C23 H23 119.91(10) . . ?
H24 C24 C23 119.91(10) . . ?
C25 C24 C23 120.18(16) . . ?
C25 C24 H24 119.91(10) . . ?
H25 C25 C24 119.95(10) . . ?
C26 C25 C24 120.09(16) . . ?
C26 C25 H25 119.95(10) . . ?
C25 C26 C21 120.07(16) . . ?
H26 C26 C21 119.97(10) . . ?
H26 C26 C25 119.97(10) . . ?
C32 C31 P1 118.64(13) . . ?
C36 C31 P1 122.41(13) . . ?
C36 C31 C32 118.91(16) . . ?
H32 C32 C31 119.73(10) . . ?
C33 C32 C31 120.53(18) . . ?
C33 C32 H32 119.73(12) . . ?
H33 C33 C32 119.82(12) . . ?
C34 C33 C32 120.4(2) . . ?
C34 C33 H33 119.82(12) . . ?
H34 C34 C33 120.08(12) . . ?
C35 C34 C33 119.85(18) . . ?
C35 C34 H34 120.08(12) . . ?
H35 C35 C34 119.74(12) . . ?
C36 C35 C34 120.53(18) . . ?
C36 C35 H35 119.74(12) . . ?
C35 C36 C31 119.78(18) . . ?
H36 C36 C31 120.11(10) . . ?
H36 C36 C35 120.11(12) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
