# 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_hanfs01_0m_sq_d
_database_code_depnum_ccdc_archive 'CCDC 1508926'
_audit_update_record             
;
2016-10-09 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H19 F5 N1 P1 S1'
_chemical_formula_sum            'C27 H19 F5 N1 P1 S1'
_chemical_formula_weight         515.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2
_symmetry_space_group_name_Hall  'C 2y'

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

_cell_length_a                   16.8922(4)
_cell_length_b                   14.6238(3)
_cell_length_c                   10.6886(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.676(1)
_cell_angle_gamma                90.00
_cell_volume                     2501.35(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    9969
_cell_measurement_theta_min      4.09
_cell_measurement_theta_max      66.58

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    2.231
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.795
_exptl_absorpt_correction_T_max  0.840
_exptl_absorpt_process_details   'SADABS, Sheldrick, 1996'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\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            12514
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_sigmaI/netI    0.0475
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.09
_diffrn_reflns_theta_max         66.58
_reflns_number_total             4366
_reflns_number_gt                3978
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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
_chemical_absolute_configuration ad
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0571P)²+1.5692P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(2)
_refine_ls_number_reflns         4366
_refine_ls_number_parameters     316
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1074
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.057
_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
S1 S 0.76682(6) 0.26815(5) 0.61417(8) 0.0365(2) Uani 1 1 d . . .
P1 P 0.75772(5) 0.35993(5) 0.73970(7) 0.02586(18) Uani 1 1 d . . .
F1 F 0.62115(13) 0.47236(17) 0.4898(2) 0.0549(6) Uani 1 1 d . . .
F2 F 0.61056(15) 0.51853(18) 0.2386(2) 0.0610(6) Uani 1 1 d . . .
F3 F 0.74956(17) 0.55132(17) 0.1771(2) 0.0606(7) Uani 1 1 d . . .
F4 F 0.90224(16) 0.5421(2) 0.3660(2) 0.0678(7) Uani 1 1 d . . .
F5 F 0.91307(12) 0.49644(16) 0.61644(19) 0.0482(5) Uani 1 1 d . . .
N1 N 0.77490(17) 0.46655(16) 0.6931(2) 0.0273(6) Uani 1 1 d . . .
C1 C 0.65850(18) 0.3587(2) 0.7697(3) 0.0282(6) Uani 1 1 d . . .
C2 C 0.5977(2) 0.2928(2) 0.7069(3) 0.0326(7) Uani 1 1 d . . .
H2 H 0.6075 0.2523 0.6439 0.039 Uiso 1 1 calc R . .
C3 C 0.5236(2) 0.2866(2) 0.7368(3) 0.0358(8) Uani 1 1 d . . .
C4 C 0.5101(2) 0.3466(3) 0.8284(4) 0.0417(8) Uani 1 1 d . . .
H4 H 0.4598 0.3427 0.8498 0.050 Uiso 1 1 calc R . .
C5 C 0.5684(2) 0.4114(3) 0.8884(4) 0.0437(9) Uani 1 1 d . . .
H5 H 0.5575 0.4525 0.9497 0.052 Uiso 1 1 calc R . .
C6 C 0.6432(2) 0.4182(2) 0.8610(3) 0.0341(7) Uani 1 1 d . . .
H6 H 0.6835 0.4629 0.9042 0.041 Uiso 1 1 calc R . .
C7 C 0.4600(3) 0.2147(3) 0.6736(4) 0.0560(11) Uani 1 1 d . . .
H7A H 0.4121 0.2204 0.7061 0.084 Uiso 1 1 calc R . .
H7B H 0.4851 0.1540 0.6960 0.084 Uiso 1 1 calc R . .
H7C H 0.4412 0.2226 0.5775 0.084 Uiso 1 1 calc R . .
C8 C 0.76682(19) 0.4856(2) 0.5589(3) 0.0263(6) Uani 1 1 d . . .
C9 C 0.6906(2) 0.4897(2) 0.4597(3) 0.0331(7) Uani 1 1 d . . .
C10 C 0.6852(2) 0.5129(2) 0.3340(3) 0.0355(8) Uani 1 1 d . . .
C11 C 0.7561(3) 0.5302(2) 0.3022(3) 0.0390(8) Uani 1 1 d . . .
C12 C 0.8322(2) 0.5247(2) 0.3966(3) 0.0383(8) Uani 1 1 d . . .
C13 C 0.8374(2) 0.5020(2) 0.5245(3) 0.0308(7) Uani 1 1 d . . .
C14 C 0.83499(18) 0.3551(2) 0.8995(3) 0.0290(6) Uani 1 1 d . . .
C15 C 0.8603(2) 0.2688(3) 0.9535(3) 0.0389(8) Uani 1 1 d . . .
H15 H 0.8350 0.2160 0.9053 0.047 Uiso 1 1 calc R . .
C16 C 0.9210(3) 0.2580(3) 1.0746(4) 0.0469(9) Uani 1 1 d . . .
C17 C 0.9582(2) 0.3375(3) 1.1417(3) 0.0451(9) Uani 1 1 d . . .
H17 H 1.0014 0.3321 1.2241 0.054 Uiso 1 1 calc R . .
C18 C 0.9334(2) 0.4235(3) 1.0907(3) 0.0392(8) Uani 1 1 d . . .
H18 H 0.9599 0.4758 1.1387 0.047 Uiso 1 1 calc R . .
C19 C 0.8695(2) 0.4352(2) 0.9684(3) 0.0303(7) Uani 1 1 d . . .
C20 C 0.84100(19) 0.5263(2) 0.9174(3) 0.0284(6) Uani 1 1 d . . .
C21 C 0.79392(19) 0.5421(2) 0.7832(3) 0.0246(6) Uani 1 1 d . . .
C22 C 0.7674(2) 0.6286(2) 0.7391(3) 0.0306(7) Uani 1 1 d . . .
H22 H 0.7369 0.6369 0.6483 0.037 Uiso 1 1 calc R . .
C23 C 0.7832(2) 0.7040(2) 0.8210(3) 0.0330(7) Uani 1 1 d . . .
C24 C 0.8286(2) 0.6899(2) 0.9529(3) 0.0389(8) Uani 1 1 d . . .
H24 H 0.8406 0.7403 1.0121 0.047 Uiso 1 1 calc R . .
C25 C 0.8569(2) 0.6031(2) 0.9998(3) 0.0348(7) Uani 1 1 d . . .
H25 H 0.8881 0.5957 1.0906 0.042 Uiso 1 1 calc R . .
C26 C 0.7532(3) 0.7976(2) 0.7720(4) 0.0450(9) Uani 1 1 d . . .
H26A H 0.7711 0.8413 0.8453 0.067 Uiso 1 1 calc R . .
H26B H 0.6921 0.7975 0.7357 0.067 Uiso 1 1 calc R . .
H26C H 0.7768 0.8154 0.7029 0.067 Uiso 1 1 calc R . .
C27 C 0.9460(4) 0.1641(3) 1.1321(5) 0.0776(16) Uani 1 1 d . . .
H27A H 0.9900 0.1697 1.2176 0.116 Uiso 1 1 calc R . .
H27B H 0.9668 0.1281 1.0718 0.116 Uiso 1 1 calc R . .
H27C H 0.8974 0.1334 1.1442 0.116 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
S1 P1 1.9384(10) . ?
P1 N1 1.690(2) . ?
P1 C14 1.788(3) . ?
P1 C1 1.804(3) . ?
F1 C9 1.337(4) . ?
F2 C10 1.345(4) . ?
F3 C11 1.342(4) . ?
F4 C12 1.349(4) . ?
F5 C13 1.343(4) . ?
N1 C8 1.425(4) . ?
N1 C21 1.433(4) . ?
C1 C6 1.392(4) . ?
C1 C2 1.411(4) . ?
C2 C3 1.391(4) . ?
C3 C4 1.386(5) . ?
C3 C7 1.501(5) . ?
C4 C5 1.369(5) . ?
C5 C6 1.388(5) . ?
C8 C13 1.376(4) . ?
C8 C9 1.382(5) . ?
C9 C10 1.360(5) . ?
C10 C11 1.369(5) . ?
C11 C12 1.359(5) . ?
C12 C13 1.383(4) . ?
C14 C15 1.397(5) . ?
C14 C19 1.407(4) . ?
C15 C16 1.379(5) . ?
C16 C17 1.406(6) . ?
C16 C27 1.508(5) . ?
C17 C18 1.381(5) . ?
C18 C19 1.414(5) . ?
C19 C20 1.462(5) . ?
C20 C25 1.398(4) . ?
C20 C21 1.418(4) . ?
C21 C22 1.375(4) . ?
C22 C23 1.380(5) . ?
C23 C24 1.387(5) . ?
C23 C26 1.495(5) . ?
C24 C25 1.393(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
N1 P1 C14 100.14(14) . . ?
N1 P1 C1 108.57(14) . . ?
C14 P1 C1 105.39(13) . . ?
N1 P1 S1 112.07(9) . . ?
C14 P1 S1 116.00(11) . . ?
C1 P1 S1 113.58(11) . . ?
C8 N1 C21 117.0(2) . . ?
C8 N1 P1 120.49(19) . . ?
C21 N1 P1 122.40(19) . . ?
C6 C1 C2 119.3(3) . . ?
C6 C1 P1 120.7(2) . . ?
C2 C1 P1 119.9(2) . . ?
C3 C2 C1 120.4(3) . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 C7 120.4(3) . . ?
C2 C3 C7 120.6(3) . . ?
C5 C4 C3 120.9(3) . . ?
C4 C5 C6 121.1(3) . . ?
C5 C6 C1 119.3(3) . . ?
C13 C8 C9 117.5(3) . . ?
C13 C8 N1 119.4(3) . . ?
C9 C8 N1 123.1(3) . . ?
F1 C9 C10 119.9(3) . . ?
F1 C9 C8 118.7(3) . . ?
C10 C9 C8 121.4(3) . . ?
F2 C10 C9 121.0(3) . . ?
F2 C10 C11 118.8(3) . . ?
C9 C10 C11 120.2(3) . . ?
F3 C11 C12 120.6(3) . . ?
F3 C11 C10 119.4(3) . . ?
C12 C11 C10 120.0(3) . . ?
F4 C12 C11 120.3(3) . . ?
F4 C12 C13 120.2(3) . . ?
C11 C12 C13 119.6(3) . . ?
F5 C13 C8 119.8(3) . . ?
F5 C13 C12 118.8(3) . . ?
C8 C13 C12 121.4(3) . . ?
C15 C14 C19 121.0(3) . . ?
C15 C14 P1 117.6(3) . . ?
C19 C14 P1 121.4(2) . . ?
C16 C15 C14 121.9(3) . . ?
C15 C16 C17 117.4(3) . . ?
C15 C16 C27 120.9(4) . . ?
C17 C16 C27 121.6(4) . . ?
C18 C17 C16 121.5(3) . . ?
C17 C18 C19 121.4(3) . . ?
C14 C19 C18 116.6(3) . . ?
C14 C19 C20 122.2(3) . . ?
C18 C19 C20 121.2(3) . . ?
C25 C20 C21 116.1(3) . . ?
C25 C20 C19 121.5(3) . . ?
C21 C20 C19 122.4(3) . . ?
C22 C21 C20 120.8(3) . . ?
C22 C21 N1 120.1(3) . . ?
C20 C21 N1 119.2(3) . . ?
C21 C22 C23 122.8(3) . . ?
C22 C23 C24 117.2(3) . . ?
C22 C23 C26 122.3(3) . . ?
C24 C23 C26 120.5(3) . . ?
C23 C24 C25 121.0(3) . . ?
C24 C25 C20 122.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        66.58
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.052
# 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 1.000 0.212 0.500 106 38 ' '
2 0.500 0.712 0.500 106 38 ' '
_platon_squeeze_details          ?
####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1539039'
_audit_update_record             
;
2017-03-20 deposited with the CCDC.
2017-05-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 F5 N O4 P'
_chemical_formula_weight         547.40

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8498(6)
_cell_length_b                   10.4837(7)
_cell_length_c                   13.4890(9)
_cell_angle_alpha                103.6640(10)
_cell_angle_beta                 110.7240(10)
_cell_angle_gamma                101.7210(10)
_cell_volume                     1201.25(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2932
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      26.05

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI_SCAN
_exptl_absorpt_correction_T_min  0.957
_exptl_absorpt_correction_T_max  0.961
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7554
_diffrn_reflns_av_unetI/netI     0.0526
_diffrn_reflns_av_R_equivalents  0.0249
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.714
_diffrn_reflns_theta_max         26.080
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4723
_reflns_number_gt                3347
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.2000P)²+1.9800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4723
_refine_ls_number_parameters     346
_refine_ls_number_restraints     16
_refine_ls_R_factor_all          0.1240
_refine_ls_R_factor_gt           0.1003
_refine_ls_wR_factor_ref         0.3219
_refine_ls_wR_factor_gt          0.2948
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.039
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.1704(8) 0.3169(7) 0.0673(7) 0.079(2) Uani 1 1 d . . . . .
H1A H 1.1385 0.3979 0.0733 0.118 Uiso 1 1 calc R U . . .
H1B H 1.2008 0.2998 0.0064 0.118 Uiso 1 1 calc R U . . .
H1C H 1.2553 0.3310 0.1363 0.118 Uiso 1 1 calc R U . . .
C2 C 0.9851(6) 0.2080(6) 0.1243(5) 0.0507(12) Uani 1 1 d . . . . .
C3 C 1.0375(6) 0.3152(6) 0.2231(5) 0.0561(13) Uani 1 1 d . . . . .
H3 H 1.1178 0.3931 0.2404 0.067 Uiso 1 1 calc R U . . .
C4 C 0.9713(6) 0.3077(5) 0.2969(4) 0.0523(13) Uani 1 1 d . . . . .
H4 H 1.0104 0.3808 0.3643 0.063 Uiso 1 1 calc R U . . .
C5 C 0.8478(5) 0.1952(5) 0.2752(4) 0.0428(11) Uani 1 1 d . . . . .
C6 C 0.7939(5) 0.0885(5) 0.1715(4) 0.0391(10) Uani 1 1 d . . . . .
C7 C 0.8628(6) 0.0925(5) 0.0985(4) 0.0460(11) Uani 1 1 d . . . . .
H7 H 0.8278 0.0185 0.0323 0.055 Uiso 1 1 calc R U . . .
C8 C 0.7803(5) 0.1971(5) 0.3576(4) 0.0427(11) Uani 1 1 d . . . . .
C9 C 0.7636(7) 0.3220(6) 0.4090(5) 0.0569(14) Uani 1 1 d . . . . .
H9 H 0.7962 0.3989 0.3902 0.068 Uiso 1 1 calc R U . . .
C10 C 0.7015(7) 0.3364(7) 0.4858(5) 0.0663(16) Uani 1 1 d . . . . .
H10 H 0.6940 0.4216 0.5190 0.100 Uiso 1 1 calc DR U . . .
C11 C 0.6497(7) 0.2217(7) 0.5137(4) 0.0614(15) Uani 1 1 d . U . . .
C12 C 0.6692(6) 0.0995(6) 0.4666(4) 0.0533(13) Uani 1 1 d . . . . .
H12 H 0.6379 0.0243 0.4876 0.064 Uiso 1 1 calc R U . . .
C13 C 0.7333(5) 0.0817(5) 0.3892(4) 0.0439(11) Uani 1 1 d . . . . .
C14 C 0.5506(14) 0.3638(12) 0.6243(10) 0.136(4) Uani 1 1 d . U . . .
H14A H 0.4919 0.3866 0.5611 0.203 Uiso 1 1 calc DR U . . .
H14B H 0.6441 0.4384 0.6711 0.203 Uiso 1 1 calc DR U . . .
H14C H 0.4926 0.3490 0.6670 0.203 Uiso 1 1 calc R U . . .
C15 C 0.7473(5) -0.0571(5) 0.3482(4) 0.0404(10) Uani 1 1 d . . . . .
C16 C 0.8147(6) -0.1173(5) 0.4273(4) 0.0483(12) Uani 1 1 d . . . . .
H16 H 0.8571 -0.0661 0.5035 0.058 Uiso 1 1 calc R U . . .
C17 C 0.8196(7) -0.2503(5) 0.3947(5) 0.0561(14) Uani 1 1 d . . . . .
H17 H 0.8659 -0.2871 0.4492 0.067 Uiso 1 1 calc R U . . .
C18 C 0.7563(6) -0.3306(5) 0.2814(5) 0.0524(13) Uani 1 1 d . . . . .
C19 C 0.6928(5) -0.2728(5) 0.2004(4) 0.0432(11) Uani 1 1 d . . . . .
H19 H 0.6532 -0.3239 0.1243 0.052 Uiso 1 1 calc R U . . .
C20 C 0.6890(5) -0.1364(5) 0.2345(4) 0.0379(10) Uani 1 1 d . . . . .
C21 C 0.6955(9) -0.5498(8) 0.1439(6) 0.086(2) Uani 1 1 d . U . . .
H21A H 0.5868 -0.5678 0.1136 0.128 Uiso 1 1 calc R U . . .
H21B H 0.7177 -0.6354 0.1399 0.128 Uiso 1 1 calc R U . . .
H21C H 0.7363 -0.5058 0.1011 0.128 Uiso 1 1 calc R U . . .
C22 C 0.3847(5) -0.0402(5) 0.1732(4) 0.0421(11) Uani 1 1 d . . . . .
C23 C 0.3389(6) 0.0558(6) 0.2310(4) 0.0515(13) Uani 1 1 d . . . . .
C24 C 0.2285(7) 0.0186(8) 0.2688(5) 0.0649(17) Uani 1 1 d . . . . .
C25 C 0.1590(7) -0.1165(8) 0.2490(5) 0.0688(18) Uani 1 1 d . . . . .
C26 C 0.2010(6) -0.2148(7) 0.1917(5) 0.0631(15) Uani 1 1 d . . . . .
C27 C 0.3115(6) -0.1785(6) 0.1525(4) 0.0499(12) Uani 1 1 d . . . . .
F1 F 0.4037(4) 0.1918(4) 0.2523(3) 0.0671(9) Uani 1 1 d . . . . .
F2 F 0.1920(5) 0.1187(5) 0.3286(4) 0.0930(14) Uani 1 1 d . . . . .
F3 F 0.0525(5) -0.1515(6) 0.2852(4) 0.1040(16) Uani 1 1 d . . . . .
F4 F 0.1310(5) -0.3477(5) 0.1683(5) 0.1025(15) Uani 1 1 d . . . . .
F5 F 0.3445(4) -0.2783(3) 0.0928(3) 0.0682(10) Uani 1 1 d . . . . .
N1 N 0.4954(4) 0.0031(4) 0.1363(3) 0.0420(9) Uani 1 1 d . . . . .
H1 H 0.4928 0.0745 0.1156 0.050 Uiso 1 1 calc R U . . .
O1 O 0.5945(4) -0.1579(3) 0.0137(3) 0.0434(8) Uani 1 1 d . . . . .
O2 O 1.0457(5) 0.2000(4) 0.0462(4) 0.0697(12) Uani 1 1 d . . . . .
O3 O 0.5868(9) 0.2342(8) 0.5831(6) 0.123(2) Uani 1 1 d . U . . .
O4 O 0.7635(6) -0.4614(4) 0.2581(3) 0.0730(13) Uani 1 1 d . U . . .
P1 P 0.63192(13) -0.06252(12) 0.12614(9) 0.0357(4) 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 O2 1.437(7) . ?
C2 C3 1.369(8) . ?
C2 O2 1.379(6) . ?
C2 C7 1.395(7) . ?
C3 C4 1.377(8) . ?
C4 C5 1.399(7) . ?
C5 C6 1.408(7) . ?
C5 C8 1.482(7) . ?
C6 C7 1.384(7) . ?
C6 P1 1.803(5) . ?
C8 C9 1.402(7) . ?
C8 C13 1.419(7) . ?
C9 C10 1.372(8) . ?
C10 C11 1.395(10) . ?
C11 O3 1.290(8) . ?
C11 C12 1.372(8) . ?
C12 C13 1.396(7) . ?
C13 C15 1.482(7) . ?
C14 O3 1.504(12) . ?
C15 C20 1.397(6) . ?
C15 C16 1.401(6) . ?
C16 C17 1.376(7) . ?
C17 C18 1.392(8) . ?
C18 O4 1.355(6) . ?
C18 C19 1.391(7) . ?
C19 C20 1.408(7) . ?
C20 P1 1.784(4) . ?
C21 O4 1.422(8) . ?
C22 C23 1.374(7) . ?
C22 N1 1.390(6) . ?
C22 C27 1.394(7) . ?
C23 F1 1.352(7) . ?
C23 C24 1.382(8) . ?
C24 F2 1.356(7) . ?
C24 C25 1.359(10) . ?
C25 F3 1.328(7) . ?
C25 C26 1.361(9) . ?
C26 F4 1.328(7) . ?
C26 C27 1.394(8) . ?
C27 F5 1.332(6) . ?
N1 P1 1.662(4) . ?
O1 P1 1.475(3) . ?

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
C3 C2 O2 125.7(5) . . ?
C3 C2 C7 119.5(5) . . ?
O2 C2 C7 114.8(5) . . ?
C2 C3 C4 120.0(5) . . ?
C3 C4 C5 123.0(5) . . ?
C4 C5 C6 115.5(4) . . ?
C4 C5 C8 119.6(4) . . ?
C6 C5 C8 124.8(4) . . ?
C7 C6 C5 122.0(4) . . ?
C7 C6 P1 115.8(4) . . ?
C5 C6 P1 122.2(4) . . ?
C6 C7 C2 119.9(5) . . ?
C9 C8 C13 117.7(5) . . ?
C9 C8 C5 117.7(5) . . ?
C13 C8 C5 124.6(4) . . ?
C10 C9 C8 123.1(6) . . ?
C9 C10 C11 119.3(5) . . ?
O3 C11 C12 122.4(7) . . ?
O3 C11 C10 119.2(6) . . ?
C12 C11 C10 118.4(5) . . ?
C11 C12 C13 123.7(5) . . ?
C12 C13 C8 117.7(5) . . ?
C12 C13 C15 116.4(5) . . ?
C8 C13 C15 125.9(4) . . ?
C20 C15 C16 117.2(4) . . ?
C20 C15 C13 124.0(4) . . ?
C16 C15 C13 118.6(4) . . ?
C17 C16 C15 121.5(5) . . ?
C16 C17 C18 120.9(5) . . ?
O4 C18 C19 124.4(5) . . ?
O4 C18 C17 116.4(4) . . ?
C19 C18 C17 119.1(5) . . ?
C18 C19 C20 119.5(4) . . ?
C15 C20 C19 121.6(4) . . ?
C15 C20 P1 121.6(4) . . ?
C19 C20 P1 116.1(3) . . ?
C23 C22 N1 119.8(5) . . ?
C23 C22 C27 116.4(5) . . ?
N1 C22 C27 123.8(4) . . ?
F1 C23 C22 119.4(5) . . ?
F1 C23 C24 118.4(5) . . ?
C22 C23 C24 122.3(6) . . ?
F2 C24 C25 119.8(6) . . ?
F2 C24 C23 119.4(6) . . ?
C25 C24 C23 120.8(6) . . ?
F3 C25 C24 120.4(7) . . ?
F3 C25 C26 120.9(7) . . ?
C24 C25 C26 118.7(5) . . ?
F4 C26 C25 119.7(6) . . ?
F4 C26 C27 119.2(6) . . ?
C25 C26 C27 121.0(6) . . ?
F5 C27 C22 120.1(5) . . ?
F5 C27 C26 119.0(5) . . ?
C22 C27 C26 120.8(5) . . ?
C22 N1 P1 129.6(3) . . ?
C2 O2 C1 117.4(5) . . ?
C11 O3 C14 121.9(7) . . ?
C18 O4 C21 118.9(5) . . ?
O1 P1 N1 115.3(2) . . ?
O1 P1 C20 113.1(2) . . ?
N1 P1 C20 108.1(2) . . ?
O1 P1 C6 112.3(2) . . ?
N1 P1 C6 103.5(2) . . ?
C20 P1 C6 103.4(2) . . ?

_refine_diff_density_max         2.808
_refine_diff_density_min         -0.736
_refine_diff_density_rms         0.116



