# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_bv4
_database_code_depnum_ccdc_archive 'CCDC 1504580'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H32 F20 K4 N4 P4'
_chemical_formula_weight         1132.90

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'
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'
K K 0.2009 0.2494 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   21.180(3)
_cell_length_b                   8.8602(13)
_cell_length_c                   24.220(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.725(2)
_cell_angle_gamma                90.00
_cell_volume                     4433.4(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    7831
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      26.65

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2272
_exptl_absorpt_coefficient_mu    0.662
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8415
_exptl_absorpt_correction_T_max  0.9015
_exptl_absorpt_process_details   SADABS-2012/1

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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            49788
_diffrn_reflns_av_R_equivalents  0.0596
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         27.25
_reflns_number_total             9935
_reflns_number_gt                7725
_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)+(0.0389P)²+4.0430P] 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         9935
_refine_ls_number_parameters     581
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1036
_refine_ls_wR_factor_gt          0.0952
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 0.23712(12) 0.1370(3) -0.05388(10) 0.0171(5) Uani 1 1 d . . .
C2 C 0.16957(12) 0.1374(3) -0.06721(11) 0.0232(6) Uani 1 1 d . . .
H2 H 0.1468 0.1972 -0.0454 0.028 Uiso 1 1 calc R . .
C3 C 0.13506(13) 0.0517(3) -0.11172(12) 0.0299(6) Uani 1 1 d . . .
H3 H 0.0891 0.0532 -0.1201 0.036 Uiso 1 1 calc R . .
C4 C 0.16735(14) -0.0354(3) -0.14377(12) 0.0308(7) Uani 1 1 d . . .
H4 H 0.1438 -0.0948 -0.1741 0.037 Uiso 1 1 calc R . .
C5 C 0.23396(14) -0.0357(3) -0.13158(11) 0.0274(6) Uani 1 1 d . . .
H5 H 0.2564 -0.0950 -0.1538 0.033 Uiso 1 1 calc R . .
C6 C 0.26848(13) 0.0496(3) -0.08721(11) 0.0218(6) Uani 1 1 d . . .
H6 H 0.3144 0.0484 -0.0794 0.026 Uiso 1 1 calc R . .
C7 C 0.12024(12) -0.0899(3) 0.12569(11) 0.0200(5) Uani 1 1 d . . .
C8 C 0.07554(13) -0.1943(3) 0.13724(12) 0.0245(6) Uani 1 1 d . . .
H8 H 0.0778 -0.2256 0.1751 0.029 Uiso 1 1 calc R . .
C9 C 0.02775(14) -0.2527(3) 0.09387(13) 0.0310(7) Uani 1 1 d . . .
H9 H -0.0026 -0.3233 0.1023 0.037 Uiso 1 1 calc R . .
C10 C 0.02406(15) -0.2087(3) 0.03847(13) 0.0338(7) Uani 1 1 d . . .
H10 H -0.0086 -0.2490 0.0088 0.041 Uiso 1 1 calc R . .
C11 C 0.06821(14) -0.1058(3) 0.02661(12) 0.0324(7) Uani 1 1 d . . .
H11 H 0.0659 -0.0754 -0.0114 0.039 Uiso 1 1 calc R . .
C12 C 0.11561(13) -0.0467(3) 0.06950(11) 0.0246(6) Uani 1 1 d . . .
H12 H 0.1455 0.0243 0.0607 0.029 Uiso 1 1 calc R . .
C13 C 0.50119(12) -0.0588(3) 0.29568(11) 0.0226(6) Uani 1 1 d . . .
C14 C 0.48218(15) -0.1732(3) 0.32881(12) 0.0321(7) Uani 1 1 d . . .
H14 H 0.4423 -0.2241 0.3150 0.039 Uiso 1 1 calc R . .
C15 C 0.51957(18) -0.2136(4) 0.38058(14) 0.0478(9) Uani 1 1 d . . .
H15 H 0.5057 -0.2911 0.4023 0.057 Uiso 1 1 calc R . .
C16 C 0.57582(18) -0.1423(5) 0.40000(15) 0.0506(10) Uani 1 1 d . . .
H16 H 0.6015 -0.1713 0.4357 0.061 Uiso 1 1 calc R . .
C17 C 0.59794(15) -0.0290(5) 0.37048(16) 0.0521(11) Uani 1 1 d . . .
H17 H 0.6379 0.0198 0.3856 0.063 Uiso 1 1 calc R . .
C18 C 0.55928(14) 0.0143(4) 0.31620(14) 0.0386(8) Uani 1 1 d . . .
H18 H 0.5735 0.0920 0.2948 0.046 Uiso 1 1 calc R . .
C19 C 0.45605(13) 0.4761(3) 0.20217(11) 0.0196(5) Uani 1 1 d . . .
C20 C 0.51489(13) 0.4895(3) 0.24561(12) 0.0302(7) Uani 1 1 d . . .
H20A H 0.5217 0.5954 0.2571 0.045 Uiso 1 1 calc R . .
H20B H 0.5517 0.4538 0.2307 0.045 Uiso 1 1 calc R . .
H20C H 0.5111 0.4283 0.2784 0.045 Uiso 1 1 calc R . .
C21 C 0.56688(14) -0.2705(3) 0.14100(12) 0.0247(6) Uani 1 1 d . . .
C22 C 0.62539(14) -0.2199(4) 0.18017(14) 0.0397(8) Uani 1 1 d . . .
H22A H 0.6143 -0.1413 0.2049 0.059 Uiso 1 1 calc R . .
H22B H 0.6557 -0.1788 0.1588 0.059 Uiso 1 1 calc R . .
H22C H 0.6455 -0.3053 0.2032 0.059 Uiso 1 1 calc R . .
C23 C 0.18077(14) 0.4743(3) 0.10412(12) 0.0254(6) Uani 1 1 d . . .
C24 C 0.12123(14) 0.4234(4) 0.06632(13) 0.0350(7) Uani 1 1 d . . .
H24A H 0.1179 0.4682 0.0288 0.053 Uiso 1 1 calc R . .
H24B H 0.0840 0.4547 0.0815 0.053 Uiso 1 1 calc R . .
H24C H 0.1217 0.3132 0.0633 0.053 Uiso 1 1 calc R . .
C25 C 0.29193(13) 0.7457(3) 0.04470(11) 0.0196(5) Uani 1 1 d . . .
C26 C 0.23063(13) 0.7543(3) 0.00398(13) 0.0301(7) Uani 1 1 d . . .
H26A H 0.2302 0.8440 -0.0198 0.045 Uiso 1 1 calc R . .
H26B H 0.1953 0.7608 0.0241 0.045 Uiso 1 1 calc R . .
H26C H 0.2250 0.6638 -0.0199 0.045 Uiso 1 1 calc R . .
C27 C 0.62669(12) 0.3008(3) 0.12760(10) 0.0179(5) Uani 1 1 d . . .
C28 C 0.67352(13) 0.4017(3) 0.11756(12) 0.0247(6) Uani 1 1 d . . .
H28 H 0.6718 0.4354 0.0800 0.030 Uiso 1 1 calc R . .
C29 C 0.72246(14) 0.4535(3) 0.16124(13) 0.0325(7) Uani 1 1 d . . .
H29 H 0.7542 0.5212 0.1536 0.039 Uiso 1 1 calc R . .
C30 C 0.72478(14) 0.4057(3) 0.21633(13) 0.0332(7) Uani 1 1 d . . .
H30 H 0.7579 0.4419 0.2465 0.040 Uiso 1 1 calc R . .
C31 C 0.67919(14) 0.3061(3) 0.22721(12) 0.0301(7) Uani 1 1 d . . .
H31 H 0.6810 0.2732 0.2649 0.036 Uiso 1 1 calc R . .
C32 C 0.63047(13) 0.2535(3) 0.18326(11) 0.0225(6) Uani 1 1 d . . .
H32 H 0.5993 0.1845 0.1912 0.027 Uiso 1 1 calc R . .
F1 F 0.32264(8) 0.33222(19) 0.06347(6) 0.0315(4) Uani 1 1 d . . .
F2 F 0.23919(9) 0.39275(17) -0.00953(7) 0.0370(4) Uani 1 1 d . . .
F3 F 0.23436(8) 0.18796(19) 0.04738(7) 0.0317(4) Uani 1 1 d . . .
F5 F 0.33494(8) 0.3049(2) -0.02617(7) 0.0378(4) Uani 1 1 d . . .
F7 F 0.24049(7) -0.04553(16) 0.14859(6) 0.0218(3) Uani 1 1 d . . .
F10 F 0.19697(8) -0.17267(18) 0.21499(6) 0.0290(4) Uani 1 1 d . . .
F8 F 0.17452(7) 0.15817(16) 0.15480(7) 0.0302(4) Uani 1 1 d . . .
F13 F 0.50839(8) 0.00435(18) 0.19610(7) 0.0306(4) Uani 1 1 d . . .
F12 F 0.45093(10) 0.16713(18) 0.24051(7) 0.0404(5) Uani 1 1 d . . .
F14 F 0.44125(7) -0.18713(16) 0.20801(6) 0.0257(3) Uani 1 1 d . . .
F15 F 0.38342(7) -0.02503(19) 0.25156(7) 0.0311(4) Uani 1 1 d . . .
F11 F 0.40103(9) 0.0301(2) 0.16542(7) 0.0412(5) Uani 1 1 d . . .
F9 F 0.13033(8) 0.03126(19) 0.22044(7) 0.0333(4) Uani 1 1 d . . .
F6 F 0.23681(9) 0.0627(2) 0.23102(8) 0.0450(5) Uani 1 1 d . . .
F4 F 0.32878(8) 0.09770(19) 0.02920(7) 0.0342(4) Uani 1 1 d . . .
F16 F 0.50487(7) 0.17088(18) 0.01802(6) 0.0275(4) Uani 1 1 d . . .
F17 F 0.54774(7) 0.40100(16) 0.04260(6) 0.0210(3) Uani 1 1 d . . .
F20 F 0.50626(7) 0.25727(16) 0.10536(6) 0.0206(3) Uani 1 1 d . . .
F18 F 0.61190(7) 0.20314(17) 0.02840(6) 0.0261(4) Uani 1 1 d . . .
F19 F 0.57126(7) 0.05805(15) 0.09207(6) 0.0217(3) Uani 1 1 d . . .
K1 K 0.42507(3) 0.48841(6) 0.05273(2) 0.01753(12) Uani 1 1 d . . .
K2 K 0.31762(3) -0.27921(6) 0.19173(2) 0.01955(12) Uani 1 1 d . . .
K3 K 0.44160(3) -0.04102(6) 0.07166(2) 0.01839(12) Uani 1 1 d . . .
K4 K 0.30919(3) 0.24132(6) 0.17065(2) 0.02228(13) Uani 1 1 d . . .
N1 N 0.22741(12) 0.5130(3) 0.13336(11) 0.0302(5) Uani 1 1 d . . .
N2 N 0.34010(11) 0.7369(2) 0.07649(10) 0.0251(5) Uani 1 1 d . . .
N3 N 0.40942(11) 0.4659(2) 0.16854(9) 0.0232(5) Uani 1 1 d . . .
N4 N 0.52053(11) -0.3091(2) 0.11114(10) 0.0258(5) Uani 1 1 d . . .
P1 P 0.28211(3) 0.24191(7) 0.00778(3) 0.01833(14) Uani 1 1 d . . .
P2 P 0.18278(3) -0.01014(8) 0.18250(3) 0.02130(15) Uani 1 1 d . . .
P3 P 0.44874(3) -0.01066(7) 0.22724(3) 0.01806(14) Uani 1 1 d . . .
P4 P 0.56235(3) 0.23163(7) 0.06965(3) 0.01630(14) 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 C6 1.389(3) . ?
C1 C2 1.396(3) . ?
C1 P1 1.837(3) . ?
C2 C3 1.388(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.395(4) . ?
C7 C12 1.396(4) . ?
C7 P2 1.829(3) . ?
C8 C9 1.389(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.383(4) . ?
C9 H9 0.9500 . ?
C10 C11 1.381(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.382(4) . ?
C13 C14 1.406(4) . ?
C13 P3 1.831(3) . ?
C14 C15 1.375(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.339(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.373(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.439(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 N3 1.137(3) . ?
C19 C20 1.448(4) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 N4 1.136(3) . ?
C21 C22 1.456(4) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 N1 1.134(4) . ?
C23 C24 1.457(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 N2 1.137(3) . ?
C25 C26 1.449(4) . ?
C25 K2 3.489(3) 1_565 ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.395(4) . ?
C27 C32 1.397(3) . ?
C27 P4 1.833(3) . ?
C28 C29 1.386(4) . ?
C28 H28 0.9500 . ?
C29 C30 1.390(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.376(4) . ?
C30 H30 0.9500 . ?
C31 C32 1.390(4) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
F1 P1 1.6391(16) . ?
F2 P1 1.6187(17) . ?
F3 P1 1.6121(16) . ?
F5 P1 1.6263(16) . ?
F7 P2 1.6460(15) . ?
F10 P2 1.6367(17) . ?
F10 K4 2.9033(16) 2_545 ?
F8 P2 1.6287(16) . ?
F13 P3 1.6132(16) . ?
F12 P3 1.6064(17) . ?
F14 P3 1.6292(16) . ?
F15 P3 1.6236(17) . ?
F11 P3 1.6512(17) . ?
F9 P2 1.6318(16) . ?
F9 K2 2.7436(17) 2 ?
F6 P2 1.5857(19) . ?
F6 K2 2.7825(19) 2 ?
F4 P1 1.6288(17) . ?
F16 P4 1.6323(16) . ?
F16 K3 2.9004(16) 3_655 ?
F17 P4 1.6394(15) . ?
F17 K1 2.6849(15) 3_665 ?
F20 P4 1.6321(15) . ?
F18 P4 1.6203(15) . ?
F18 K3 2.8301(16) 3_655 ?
F18 K1 3.3563(17) 3_665 ?
F19 P4 1.6281(15) . ?
K1 F17 2.6848(15) 3_665 ?
K1 N4 2.837(2) 1_565 ?
K1 F18 3.3563(17) 3_665 ?
K1 K3 4.2007(9) 1_565 ?
K1 K1 4.4958(11) 3_665 ?
K1 K2 4.9121(9) 1_565 ?
K2 F9 2.7436(16) 2_545 ?
K2 F6 2.7824(19) 2_545 ?
K2 N1 2.802(2) 1_545 ?
K2 N2 2.937(2) 1_545 ?
K2 N3 3.111(2) 1_545 ?
K2 C25 3.489(3) 1_545 ?
K2 P2 3.6711(9) 2_545 ?
K2 K4 4.2778(10) 1_545 ?
K2 K4 4.7223(9) 2_545 ?
K2 K1 4.9121(9) 1_545 ?
K3 F18 2.8302(16) 3_655 ?
K3 F16 2.9004(16) 3_655 ?
K3 N2 2.936(2) 1_545 ?
K3 P4 3.8008(9) 3_655 ?
K3 K1 4.2007(9) 1_545 ?
K3 K3 4.7413(12) 3_655 ?
K4 F10 2.9033(16) 2 ?
K4 K2 4.2778(10) 1_565 ?
K4 K2 4.7222(9) 2 ?
N1 K2 2.802(2) 1_565 ?
N2 K3 2.936(2) 1_565 ?
N2 K2 2.937(2) 1_565 ?
N3 K2 3.111(2) 1_565 ?
N4 K1 2.837(2) 1_545 ?
P2 K2 3.6710(9) 2 ?
P4 K3 3.8007(9) 3_655 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 117.6(2) . . ?
C6 C1 P1 121.72(19) . . ?
C2 C1 P1 120.59(19) . . ?
C3 C2 C1 121.1(2) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.5(3) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 121.2(2) . . ?
C5 C6 H6 119.4 . . ?
C1 C6 H6 119.4 . . ?
C8 C7 C12 118.2(3) . . ?
C8 C7 P2 121.1(2) . . ?
C12 C7 P2 120.7(2) . . ?
C9 C8 C7 120.6(3) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C10 C9 C8 120.3(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.5(3) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C7 120.9(3) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C18 C13 C14 118.5(3) . . ?
C18 C13 P3 122.1(2) . . ?
C14 C13 P3 119.5(2) . . ?
C15 C14 C13 121.9(3) . . ?
C15 C14 H14 119.1 . . ?
C13 C14 H14 119.1 . . ?
C16 C15 C14 119.1(4) . . ?
C16 C15 H15 120.4 . . ?
C14 C15 H15 120.4 . . ?
C15 C16 C17 122.8(3) . . ?
C15 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C16 C17 C18 118.7(3) . . ?
C16 C17 H17 120.7 . . ?
C18 C17 H17 120.7 . . ?
C13 C18 C17 119.1(3) . . ?
C13 C18 H18 120.5 . . ?
C17 C18 H18 120.5 . . ?
N3 C19 C20 179.2(3) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N4 C21 C22 178.7(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 C24 179.4(3) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N2 C25 C26 179.1(3) . . ?
N2 C25 K2 52.40(16) . 1_565 ?
C26 C25 K2 127.79(18) . 1_565 ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C32 117.9(2) . . ?
C28 C27 P4 121.2(2) . . ?
C32 C27 P4 120.89(19) . . ?
C29 C28 C27 121.3(3) . . ?
C29 C28 H28 119.3 . . ?
C27 C28 H28 119.3 . . ?
C28 C29 C30 119.6(3) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C31 C30 C29 120.1(3) . . ?
C31 C30 H30 120.0 . . ?
C29 C30 H30 120.0 . . ?
C30 C31 C32 120.2(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C31 C32 C27 120.9(3) . . ?
C31 C32 H32 119.6 . . ?
C27 C32 H32 119.6 . . ?
P2 F10 K4 130.36(8) . 2_545 ?
P2 F9 K2 111.53(8) . 2 ?
P2 F6 K2 111.40(9) . 2 ?
P4 F16 K3 110.84(8) . 3_655 ?
P4 F17 K1 128.34(8) . 3_665 ?
P4 F18 K3 114.55(8) . 3_655 ?
P4 F18 K1 97.75(7) . 3_665 ?
K3 F18 K1 85.08(4) 3_655 3_665 ?
F17 K1 N4 86.20(6) 3_665 1_565 ?
F17 K1 F18 42.77(4) 3_665 3_665 ?
N4 K1 F18 79.96(5) 1_565 3_665 ?
F17 K1 K3 72.73(3) 3_665 1_565 ?
N4 K1 K3 44.34(5) 1_565 1_565 ?
F18 K1 K3 42.16(3) 3_665 1_565 ?
F17 K1 K1 35.19(3) 3_665 3_665 ?
N4 K1 K1 74.91(5) 1_565 3_665 ?
F18 K1 K1 74.52(3) 3_665 3_665 ?
K3 K1 K1 87.957(16) 1_565 3_665 ?
F17 K1 K2 130.99(4) 3_665 1_565 ?
N4 K1 K2 77.29(5) 1_565 1_565 ?
F18 K1 K2 88.65(3) 3_665 1_565 ?
K3 K1 K2 63.206(12) 1_565 1_565 ?
K1 K1 K2 149.53(2) 3_665 1_565 ?
F9 K2 F6 47.60(5) 2_545 2_545 ?
F9 K2 N1 95.85(7) 2_545 1_545 ?
F6 K2 N1 70.79(7) 2_545 1_545 ?
F9 K2 N2 130.17(6) 2_545 1_545 ?
F6 K2 N2 147.30(6) 2_545 1_545 ?
N1 K2 N2 77.74(7) 1_545 1_545 ?
F9 K2 N3 62.31(5) 2_545 1_545 ?
F6 K2 N3 97.12(6) 2_545 1_545 ?
N1 K2 N3 79.38(7) 1_545 1_545 ?
N2 K2 N3 67.97(6) 1_545 1_545 ?
F9 K2 C25 140.87(6) 2_545 1_545 ?
F6 K2 C25 136.35(6) 2_545 1_545 ?
N1 K2 C25 65.84(7) 1_545 1_545 ?
N2 K2 C25 17.87(6) 1_545 1_545 ?
N3 K2 C25 79.90(6) 1_545 1_545 ?
F9 K2 P2 24.42(3) 2_545 2_545 ?
F6 K2 P2 23.71(4) 2_545 2_545 ?
N1 K2 P2 85.78(5) 1_545 2_545 ?
N2 K2 P2 147.81(5) 1_545 2_545 ?
N3 K2 P2 82.01(4) 1_545 2_545 ?
C25 K2 P2 148.63(4) 1_545 2_545 ?
F9 K2 K4 58.92(4) 2_545 1_545 ?
F6 K2 K4 64.39(4) 2_545 1_545 ?
N1 K2 K4 44.05(5) 1_545 1_545 ?
N2 K2 K4 86.90(5) 1_545 1_545 ?
N3 K2 K4 43.02(4) 1_545 1_545 ?
C25 K2 K4 87.01(4) 1_545 1_545 ?
P2 K2 K4 62.478(17) 2_545 1_545 ?
F9 K2 K4 70.74(4) 2_545 2_545 ?
F6 K2 K4 32.91(4) 2_545 2_545 ?
N1 K2 K4 87.18(5) 1_545 2_545 ?
N2 K2 K4 154.89(5) 1_545 2_545 ?
N3 K2 K4 129.10(4) 1_545 2_545 ?
C25 K2 K4 137.13(5) 1_545 2_545 ?
P2 K2 K4 47.947(15) 2_545 2_545 ?
K4 K2 K4 96.157(14) 1_545 2_545 ?
F9 K2 K1 96.15(4) 2_545 1_545 ?
F6 K2 K1 124.96(4) 2_545 1_545 ?
N1 K2 K1 75.29(5) 1_545 1_545 ?
N2 K2 K1 34.14(5) 1_545 1_545 ?
N3 K2 K1 33.86(4) 1_545 1_545 ?
C25 K2 K1 47.04(4) 1_545 1_545 ?
P2 K2 K1 114.910(19) 2_545 1_545 ?
K4 K2 K1 61.011(12) 1_545 1_545 ?
K4 K2 K1 157.118(16) 2_545 1_545 ?
F18 K3 F16 46.07(4) 3_655 3_655 ?
F18 K3 N2 62.31(5) 3_655 1_545 ?
F16 K3 N2 100.04(6) 3_655 1_545 ?
F18 K3 P4 22.82(3) 3_655 3_655 ?
F16 K3 P4 23.66(3) 3_655 3_655 ?
N2 K3 P4 82.35(5) 1_545 3_655 ?
F18 K3 K1 52.75(3) 3_655 1_545 ?
F16 K3 K1 63.99(3) 3_655 1_545 ?
N2 K3 K1 45.16(5) 1_545 1_545 ?
P4 K3 K1 58.394(14) 3_655 1_545 ?
F18 K3 K3 68.04(3) 3_655 3_655 ?
F16 K3 K3 32.81(3) 3_655 3_655 ?
N2 K3 K3 129.54(5) 1_545 3_655 ?
P4 K3 K3 47.191(15) 3_655 3_655 ?
K1 K3 K3 96.700(17) 1_545 3_655 ?
F10 K4 K2 68.59(3) 2 1_565 ?
F10 K4 K2 35.38(3) 2 2 ?
K2 K4 K2 88.239(14) 1_565 2 ?
C23 N1 K2 156.5(2) . 1_565 ?
C25 N2 K3 118.86(19) . 1_565 ?
C25 N2 K2 109.73(19) . 1_565 ?
K3 N2 K2 110.12(8) 1_565 1_565 ?
C19 N3 K2 106.97(18) . 1_565 ?
C21 N4 K1 158.2(2) . 1_545 ?
F3 P1 F2 90.50(10) . . ?
F3 P1 F5 173.86(9) . . ?
F2 P1 F5 89.74(10) . . ?
F3 P1 F4 89.66(9) . . ?
F2 P1 F4 175.52(10) . . ?
F5 P1 F4 89.62(10) . . ?
F3 P1 F1 86.48(8) . . ?
F2 P1 F1 88.42(9) . . ?
F5 P1 F1 87.40(8) . . ?
F4 P1 F1 87.12(9) . . ?
F3 P1 C1 93.02(10) . . ?
F2 P1 C1 92.63(10) . . ?
F5 P1 C1 93.10(10) . . ?
F4 P1 C1 91.83(10) . . ?
F1 P1 C1 178.84(11) . . ?
F6 P2 F8 85.82(10) . . ?
F6 P2 F9 87.76(9) . . ?
F8 P2 F9 90.08(9) . . ?
F6 P2 F10 88.60(10) . . ?
F8 P2 F10 174.40(10) . . ?
F9 P2 F10 90.16(9) . . ?
F6 P2 F7 87.32(9) . . ?
F8 P2 F7 89.61(8) . . ?
F9 P2 F7 175.08(9) . . ?
F10 P2 F7 89.68(8) . . ?
F6 P2 C7 178.68(12) . . ?
F8 P2 C7 92.86(10) . . ?
F9 P2 C7 92.32(10) . . ?
F10 P2 C7 92.72(10) . . ?
F7 P2 C7 92.60(10) . . ?
F6 P2 K2 44.89(7) . 2 ?
F8 P2 K2 79.15(6) . 2 ?
F9 P2 K2 44.04(6) . 2 ?
F10 P2 K2 97.19(6) . 2 ?
F7 P2 K2 131.14(6) . 2 ?
C7 P2 K2 134.92(8) . 2 ?
F12 P3 F13 91.24(9) . . ?
F12 P3 F15 89.64(10) . . ?
F13 P3 F15 173.57(9) . . ?
F12 P3 F14 174.29(10) . . ?
F13 P3 F14 88.99(8) . . ?
F15 P3 F14 89.51(9) . . ?
F12 P3 F11 87.23(10) . . ?
F13 P3 F11 86.78(9) . . ?
F15 P3 F11 86.90(9) . . ?
F14 P3 F11 87.09(9) . . ?
F12 P3 C13 93.57(11) . . ?
F13 P3 C13 93.50(11) . . ?
F15 P3 C13 92.80(10) . . ?
F14 P3 C13 92.11(10) . . ?
F11 P3 C13 179.15(12) . . ?
F18 P4 F19 90.87(8) . . ?
F18 P4 F20 173.95(9) . . ?
F19 P4 F20 89.95(8) . . ?
F18 P4 F16 87.22(8) . . ?
F19 P4 F16 87.49(8) . . ?
F20 P4 F16 86.83(8) . . ?
F18 P4 F17 89.26(8) . . ?
F19 P4 F17 174.75(9) . . ?
F20 P4 F17 89.37(8) . . ?
F16 P4 F17 87.28(8) . . ?
F18 P4 C27 92.92(10) . . ?
F19 P4 C27 92.78(10) . . ?
F20 P4 C27 93.03(10) . . ?
F16 P4 C27 179.70(11) . . ?
F17 P4 C27 92.45(10) . . ?
F18 P4 K3 42.64(6) . 3_655 ?
F19 P4 K3 81.87(6) . 3_655 ?
F20 P4 K3 131.67(6) . 3_655 ?
F16 P4 K3 45.49(6) . 3_655 ?
F17 P4 K3 94.71(6) . 3_655 ?
C27 P4 K3 134.69(8) . 3_655 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.8(4) . . . . ?
P1 C1 C2 C3 -176.3(2) . . . . ?
C1 C2 C3 C4 -0.1(4) . . . . ?
C2 C3 C4 C5 -0.6(4) . . . . ?
C3 C4 C5 C6 0.5(4) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
P1 C1 C6 C5 176.2(2) . . . . ?
C12 C7 C8 C9 -0.2(4) . . . . ?
P2 C7 C8 C9 179.2(2) . . . . ?
C7 C8 C9 C10 0.3(4) . . . . ?
C8 C9 C10 C11 -0.2(5) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 C7 0.3(4) . . . . ?
C8 C7 C12 C11 -0.1(4) . . . . ?
P2 C7 C12 C11 -179.5(2) . . . . ?
C18 C13 C14 C15 0.1(4) . . . . ?
P3 C13 C14 C15 -179.8(2) . . . . ?
C13 C14 C15 C16 -0.2(5) . . . . ?
C14 C15 C16 C17 0.4(5) . . . . ?
C15 C16 C17 C18 -0.4(5) . . . . ?
C14 C13 C18 C17 -0.1(4) . . . . ?
P3 C13 C18 C17 179.7(2) . . . . ?
C16 C17 C18 C13 0.3(5) . . . . ?
C32 C27 C28 C29 0.1(4) . . . . ?
P4 C27 C28 C29 -179.6(2) . . . . ?
C27 C28 C29 C30 -0.7(4) . . . . ?
C28 C29 C30 C31 0.8(4) . . . . ?
C29 C30 C31 C32 -0.4(4) . . . . ?
C30 C31 C32 C27 -0.2(4) . . . . ?
C28 C27 C32 C31 0.4(4) . . . . ?
P4 C27 C32 C31 -179.9(2) . . . . ?
C24 C23 N1 K2 139(100) . . . 1_565 ?
C26 C25 N2 K3 130(18) . . . 1_565 ?
K2 C25 N2 K3 -127.9(2) 1_565 . . 1_565 ?
C26 C25 N2 K2 -102(18) . . . 1_565 ?
C20 C19 N3 K2 43(20) . . . 1_565 ?
C22 C21 N4 K1 -107(14) . . . 1_545 ?
C6 C1 P1 F3 -134.5(2) . . . . ?
C2 C1 P1 F3 42.5(2) . . . . ?
C6 C1 P1 F2 134.8(2) . . . . ?
C2 C1 P1 F2 -48.2(2) . . . . ?
C6 C1 P1 F5 44.9(2) . . . . ?
C2 C1 P1 F5 -138.1(2) . . . . ?
C6 C1 P1 F4 -44.8(2) . . . . ?
C2 C1 P1 F4 132.2(2) . . . . ?
C6 C1 P1 F1 -70(5) . . . . ?
C2 C1 P1 F1 107(5) . . . . ?
K2 F6 P2 F8 78.81(9) 2 . . . ?
K2 F6 P2 F9 -11.44(10) 2 . . . ?
K2 F6 P2 F10 -101.65(10) 2 . . . ?
K2 F6 P2 F7 168.61(9) 2 . . . ?
K2 F6 P2 C7 82(5) 2 . . . ?
K2 F9 P2 F6 11.61(10) 2 . . . ?
K2 F9 P2 F8 -74.20(9) 2 . . . ?
K2 F9 P2 F10 100.21(9) 2 . . . ?
K2 F9 P2 F7 12.2(11) 2 . . . ?
K2 F9 P2 C7 -167.06(10) 2 . . . ?
K4 F10 P2 F6 57.65(12) 2_545 . . . ?
K4 F10 P2 F8 62.3(10) 2_545 . . . ?
K4 F10 P2 F9 -30.11(12) 2_545 . . . ?
K4 F10 P2 F7 144.98(10) 2_545 . . . ?
K4 F10 P2 C7 -122.43(12) 2_545 . . . ?
K4 F10 P2 K2 13.49(10) 2_545 . . 2 ?
C8 C7 P2 F6 -142(5) . . . . ?
C12 C7 P2 F6 37(5) . . . . ?
C8 C7 P2 F8 -139.2(2) . . . . ?
C12 C7 P2 F8 40.2(2) . . . . ?
C8 C7 P2 F9 -49.0(2) . . . . ?
C12 C7 P2 F9 130.4(2) . . . . ?
C8 C7 P2 F10 41.3(2) . . . . ?
C12 C7 P2 F10 -139.4(2) . . . . ?
C8 C7 P2 F7 131.1(2) . . . . ?
C12 C7 P2 F7 -49.6(2) . . . . ?
C8 C7 P2 K2 -61.7(2) . . . 2 ?
C12 C7 P2 K2 117.66(19) . . . 2 ?
C18 C13 P3 F12 -49.6(2) . . . . ?
C14 C13 P3 F12 130.3(2) . . . . ?
C18 C13 P3 F13 41.9(2) . . . . ?
C14 C13 P3 F13 -138.3(2) . . . . ?
C18 C13 P3 F15 -139.4(2) . . . . ?
C14 C13 P3 F15 40.5(2) . . . . ?
C18 C13 P3 F14 131.0(2) . . . . ?
C14 C13 P3 F14 -49.2(2) . . . . ?
C18 C13 P3 F11 151(7) . . . . ?
C14 C13 P3 F11 -29(8) . . . . ?
K3 F18 P4 F19 76.97(8) 3_655 . . . ?
K1 F18 P4 F19 165.09(6) 3_665 . . . ?
K3 F18 P4 F20 -20.9(9) 3_655 . . . ?
K1 F18 P4 F20 67.2(8) 3_665 . . . ?
K3 F18 P4 F16 -10.47(9) 3_655 . . . ?
K1 F18 P4 F16 77.64(7) 3_665 . . . ?
K3 F18 P4 F17 -97.78(8) 3_655 . . . ?
K1 F18 P4 F17 -9.67(7) 3_665 . . . ?
K3 F18 P4 C27 169.80(10) 3_655 . . . ?
K1 F18 P4 C27 -102.09(8) 3_665 . . . ?
K1 F18 P4 K3 88.11(7) 3_665 . . 3_655 ?
K3 F16 P4 F18 9.94(8) 3_655 . . . ?
K3 F16 P4 F19 -81.06(8) 3_655 . . . ?
K3 F16 P4 F20 -171.15(8) 3_655 . . . ?
K3 F16 P4 F17 99.33(8) 3_655 . . . ?
K3 F16 P4 C27 127(21) 3_655 . . . ?
K1 F17 P4 F18 15.38(10) 3_665 . . . ?
K1 F17 P4 F19 -76.1(9) 3_665 . . . ?
K1 F17 P4 F20 -158.73(10) 3_665 . . . ?
K1 F17 P4 F16 -71.87(10) 3_665 . . . ?
K1 F17 P4 C27 108.27(11) 3_665 . . . ?
K1 F17 P4 K3 -26.95(9) 3_665 . . 3_655 ?
C28 C27 P4 F18 43.9(2) . . . . ?
C32 C27 P4 F18 -135.8(2) . . . . ?
C28 C27 P4 F19 134.9(2) . . . . ?
C32 C27 P4 F19 -44.8(2) . . . . ?
C28 C27 P4 F20 -135.0(2) . . . . ?
C32 C27 P4 F20 45.3(2) . . . . ?
C28 C27 P4 F16 -73(21) . . . . ?
C32 C27 P4 F16 107(21) . . . . ?
C28 C27 P4 F17 -45.5(2) . . . . ?
C32 C27 P4 F17 134.8(2) . . . . ?
C28 C27 P4 K3 53.6(2) . . . 3_655 ?
C32 C27 P4 K3 -126.13(18) . . . 3_655 ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.25
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.887
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_data
_database_code_depnum_ccdc_archive 'CCDC 1504579'
_audit_update_record             
;
2016-09-16 deposited with the CCDC.
2017-07-11 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H13 F4 N2 P'
_chemical_formula_sum            'C11 H13 F4 N2 P'
_chemical_formula_weight         280.20

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'
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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/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                   7.5298(13)
_cell_length_b                   11.1769(19)
_cell_length_c                   14.477(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.313(2)
_cell_angle_gamma                90.00
_cell_volume                     1180.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3243
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.92

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9386
_exptl_absorpt_correction_T_max  0.9435
_exptl_absorpt_process_details   SADABS-2012/1

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      110(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            11492
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_sigmaI/netI    0.0337
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         28.29
_reflns_number_total             2921
_reflns_number_gt                2462
_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)+(0.0527P)²+0.1800P] 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         2921
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_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
P1 P 0.22848(5) 0.75320(3) 0.39213(2) 0.01450(11) Uani 1 1 d . . .
N2 N 0.53113(17) 0.91806(10) 0.39740(8) 0.0196(3) Uani 1 1 d . . .
N1 N 0.61364(17) 0.77093(10) 0.49487(8) 0.0193(3) Uani 1 1 d . . .
F1 F 0.32257(11) 0.62103(7) 0.39496(6) 0.0206(2) Uani 1 1 d . . .
F3 F 0.14840(11) 0.88886(7) 0.39210(6) 0.0238(2) Uani 1 1 d . . .
F2 F 0.24371(12) 0.76998(7) 0.28162(6) 0.0221(2) Uani 1 1 d . . .
F4 F 0.22855(12) 0.74070(7) 0.50540(6) 0.0221(2) Uani 1 1 d . . .
C11 C -0.0466(2) 0.58015(13) 0.38773(10) 0.0205(3) Uani 1 1 d . . .
H11 H 0.0443 0.5391 0.4342 0.025 Uiso 1 1 calc R . .
C6 C -0.00329(18) 0.68962(13) 0.35250(9) 0.0177(3) Uani 1 1 d . . .
C1 C 0.46853(19) 0.81786(12) 0.43090(9) 0.0168(3) Uani 1 1 d . . .
C7 C -0.1397(2) 0.74774(13) 0.28514(11) 0.0226(3) Uani 1 1 d . . .
H7 H -0.1136 0.8226 0.2603 0.027 Uiso 1 1 calc R . .
C3 C 0.7144(2) 0.93296(14) 0.43942(10) 0.0256(3) Uani 1 1 d . . .
H3 H 0.7902 0.9962 0.4276 0.031 Uiso 1 1 calc R . .
C2 C 0.4306(2) 1.00253(13) 0.32548(11) 0.0273(3) Uani 1 1 d . . .
H2A H 0.3778 0.9595 0.2660 0.041 Uiso 1 1 calc R . .
H2B H 0.5147 1.0643 0.3138 0.041 Uiso 1 1 calc R . .
H2C H 0.3321 1.0400 0.3486 0.041 Uiso 1 1 calc R . .
C8 C -0.3139(2) 0.69820(15) 0.25344(11) 0.0282(3) Uani 1 1 d . . .
H8 H -0.4054 0.7396 0.2076 0.034 Uiso 1 1 calc R . .
C10 C -0.2202(2) 0.52978(15) 0.35624(11) 0.0268(3) Uani 1 1 d . . .
H10 H -0.2468 0.4551 0.3812 0.032 Uiso 1 1 calc R . .
C5 C 0.6211(2) 0.66233(14) 0.55298(10) 0.0254(3) Uani 1 1 d . . .
H5A H 0.5155 0.6608 0.5813 0.038 Uiso 1 1 calc R . .
H5B H 0.7346 0.6622 0.6038 0.038 Uiso 1 1 calc R . .
H5C H 0.6181 0.5916 0.5127 0.038 Uiso 1 1 calc R . .
C9 C -0.3545(2) 0.58866(15) 0.28845(11) 0.0292(4) Uani 1 1 d . . .
H9 H -0.4729 0.5543 0.2663 0.035 Uiso 1 1 calc R . .
C4 C 0.7666(2) 0.84155(14) 0.50017(10) 0.0255(3) Uani 1 1 d . . .
H4 H 0.8861 0.8279 0.5394 0.031 Uiso 1 1 calc R . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 F3 1.6318(9) . ?
P1 F1 1.6344(9) . ?
P1 F2 1.6428(9) . ?
P1 F4 1.6456(9) . ?
P1 C6 1.8398(14) . ?
P1 C1 1.8981(14) . ?
N2 C1 1.3508(17) . ?
N2 C3 1.3739(19) . ?
N2 C2 1.4693(19) . ?
N1 C1 1.3515(18) . ?
N1 C4 1.3826(19) . ?
N1 C5 1.4700(18) . ?
C11 C10 1.393(2) . ?
C11 C6 1.395(2) . ?
C11 H11 0.9500 . ?
C6 C7 1.390(2) . ?
C7 C8 1.393(2) . ?
C7 H7 0.9500 . ?
C3 C4 1.342(2) . ?
C3 H3 0.9500 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C8 C9 1.388(2) . ?
C8 H8 0.9500 . ?
C10 C9 1.389(2) . ?
C10 H10 0.9500 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C9 H9 0.9500 . ?
C4 H4 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
F3 P1 F1 176.13(4) . . ?
F3 P1 F2 90.48(5) . . ?
F1 P1 F2 89.62(4) . . ?
F3 P1 F4 89.32(5) . . ?
F1 P1 F4 90.28(4) . . ?
F2 P1 F4 175.75(4) . . ?
F3 P1 C6 92.11(6) . . ?
F1 P1 C6 91.76(6) . . ?
F2 P1 C6 91.70(5) . . ?
F4 P1 C6 92.55(5) . . ?
F3 P1 C1 88.34(5) . . ?
F1 P1 C1 87.79(5) . . ?
F2 P1 C1 87.36(5) . . ?
F4 P1 C1 88.39(5) . . ?
C6 P1 C1 178.96(6) . . ?
C1 N2 C3 110.06(12) . . ?
C1 N2 C2 128.52(12) . . ?
C3 N2 C2 121.41(12) . . ?
C1 N1 C4 109.74(12) . . ?
C1 N1 C5 128.51(12) . . ?
C4 N1 C5 121.76(12) . . ?
C10 C11 C6 121.34(13) . . ?
C10 C11 H11 119.3 . . ?
C6 C11 H11 119.3 . . ?
C7 C6 C11 117.87(13) . . ?
C7 C6 P1 121.17(11) . . ?
C11 C6 P1 120.94(10) . . ?
N2 C1 N1 105.84(12) . . ?
N2 C1 P1 126.93(10) . . ?
N1 C1 P1 127.18(10) . . ?
C6 C7 C8 121.18(14) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C4 C3 N2 107.29(13) . . ?
C4 C3 H3 126.4 . . ?
N2 C3 H3 126.4 . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C9 C8 C7 120.32(14) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C9 C10 C11 120.04(15) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C10 C9 C8 119.24(14) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C3 C4 N1 107.06(13) . . ?
C3 C4 H4 126.5 . . ?
N1 C4 H4 126.5 . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.406
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.056
