# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_t1217m
_database_code_depnum_ccdc_archive 'CCDC 1444285'
_audit_update_record             
;
2015-12-25 deposited with the CCDC.
2016-06-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H11.50 F N O P'
_chemical_formula_weight         415.84

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

_symmetry_cell_setting           monoclinic

_symmetry_space_group_name_H-M   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                   12.481(3)
_cell_length_b                   10.625(2)
_cell_length_c                   17.678(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.484(3)
_cell_angle_gamma                90.00
_cell_volume                     2223.3(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5155
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      28.54

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.242
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             850
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.890297
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16752
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         26.00
_reflns_number_total             4348
_reflns_number_gt                3977
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.1000P)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         4348
_refine_ls_number_parameters     280
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0602
_refine_ls_R_factor_gt           0.0563
_refine_ls_wR_factor_ref         0.1958
_refine_ls_wR_factor_gt          0.1919
_refine_ls_goodness_of_fit_ref   1.616
_refine_ls_restrained_S_all      1.616
_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 0.95359(4) 0.54726(5) 0.22898(3) 0.0230(2) Uani 1 1 d . . .
O1 O 0.94996(13) 0.46832(14) 0.15950(9) 0.0315(4) Uani 1 1 d . . .
N1 N 1.15762(14) 0.85236(18) 0.26697(11) 0.0307(4) Uani 1 1 d . . .
C22 C 0.81736(17) 0.56657(19) 0.24033(12) 0.0247(4) Uani 1 1 d . . .
C3 C 0.94699(17) 0.78210(19) 0.15950(12) 0.0248(4) Uani 1 1 d . . .
F5 F 0.51366(13) 0.67017(18) -0.03693(9) 0.0591(5) Uani 1 1 d . . .
C4 C 0.99800(18) 0.89758(19) 0.14992(12) 0.0269(4) Uani 1 1 d . . .
C16 C 1.04564(17) 0.47678(19) 0.31808(13) 0.0266(4) Uani 1 1 d . . .
C10 C 0.83241(17) 0.75244(19) 0.10527(12) 0.0262(4) Uani 1 1 d . . .
C2 C 1.00572(16) 0.70387(18) 0.22125(12) 0.0243(4) Uani 1 1 d . . .
C11 C 0.73939(18) 0.8000(2) 0.12261(12) 0.0287(5) Uani 1 1 d . . .
H11 H 0.7500 0.8526 0.1664 0.034 Uiso 1 1 calc R . .
C9 C 1.10354(17) 0.9292(2) 0.20545(13) 0.0282(5) Uani 1 1 d . . .
C1 C 1.10962(17) 0.7448(2) 0.27251(13) 0.0290(5) Uani 1 1 d . . .
H1 H 1.1478 0.6913 0.3139 0.035 Uiso 1 1 calc R . .
C23 C 0.79828(19) 0.6490(2) 0.29536(13) 0.0311(5) Uani 1 1 d . . .
H23 H 0.8583 0.6931 0.3299 0.037 Uiso 1 1 calc R . .
C17 C 1.0624(2) 0.5218(2) 0.39483(13) 0.0348(5) Uani 1 1 d . . .
H17 H 1.0257 0.5947 0.4023 0.042 Uiso 1 1 calc R . .
C25 C 0.60247(19) 0.6013(2) 0.24701(15) 0.0382(6) Uani 1 1 d . . .
H25 H 0.5296 0.6137 0.2489 0.046 Uiso 1 1 calc R . .
C26 C 0.6207(2) 0.5190(2) 0.19258(15) 0.0375(6) Uani 1 1 d . . .
H26 H 0.5604 0.4751 0.1580 0.045 Uiso 1 1 calc R . .
C27 C 0.72811(19) 0.5013(2) 0.18917(13) 0.0302(5) Uani 1 1 d . . .
H27 H 0.7406 0.4454 0.1524 0.036 Uiso 1 1 calc R . .
C21 C 1.1009(2) 0.3676(2) 0.30896(14) 0.0333(5) Uani 1 1 d . . .
H21 H 1.0904 0.3357 0.2581 0.040 Uiso 1 1 calc R . .
C6 C 0.9973(2) 1.0936(2) 0.08172(15) 0.0376(5) Uani 1 1 d . . .
H6 H 0.9629 1.1489 0.0404 0.045 Uiso 1 1 calc R . .
C12 C 0.63224(19) 0.7704(2) 0.07590(14) 0.0346(5) Uani 1 1 d . . .
H12 H 0.5697 0.7995 0.0885 0.042 Uiso 1 1 calc R . .
C5 C 0.9465(2) 0.9838(2) 0.08832(13) 0.0323(5) Uani 1 1 d . . .
H5 H 0.8765 0.9646 0.0517 0.039 Uiso 1 1 calc R . .
C13 C 0.61953(19) 0.6972(2) 0.01055(14) 0.0381(5) Uani 1 1 d . . .
C15 C 0.8156(2) 0.6788(2) 0.03806(12) 0.0331(5) Uani 1 1 d . . .
H15 H 0.8775 0.6479 0.0254 0.040 Uiso 1 1 calc R . .
C8 C 1.1540(2) 1.0438(2) 0.19733(16) 0.0368(5) Uani 1 1 d . . .
H8 H 1.2238 1.0652 0.2334 0.044 Uiso 1 1 calc R . .
C18 C 1.1325(2) 0.4596(2) 0.45935(14) 0.0405(6) Uani 1 1 d . . .
H18 H 1.1440 0.4911 0.5104 0.049 Uiso 1 1 calc R . .
C24 C 0.6915(2) 0.6657(2) 0.29901(15) 0.0359(5) Uani 1 1 d . . .
H24 H 0.6789 0.7204 0.3364 0.043 Uiso 1 1 calc R . .
C7 C 1.1019(2) 1.1241(2) 0.13727(16) 0.0397(6) Uani 1 1 d . . .
H7 H 1.1361 1.2004 0.1329 0.048 Uiso 1 1 calc R . .
C19 C 1.1858(2) 0.3514(2) 0.44926(15) 0.0433(6) Uani 1 1 d . . .
H19 H 1.2322 0.3087 0.4934 0.052 Uiso 1 1 calc R . .
C20 C 1.1709(2) 0.3061(2) 0.37416(15) 0.0416(6) Uani 1 1 d . . .
H20 H 1.2084 0.2335 0.3673 0.050 Uiso 1 1 calc R . .
C14 C 0.7088(2) 0.6511(2) -0.00986(14) 0.0406(6) Uani 1 1 d . . .
H14 H 0.6972 0.6019 -0.0553 0.049 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 O1 1.4762(16) . ?
P1 C22 1.786(2) . ?
P1 C16 1.793(2) . ?
P1 C2 1.807(2) . ?
N1 C1 1.309(3) . ?
N1 C9 1.356(3) . ?
C22 C27 1.379(3) . ?
C22 C23 1.385(3) . ?
C3 C2 1.383(3) . ?
C3 C4 1.417(3) . ?
C3 C10 1.481(3) . ?
F5 C13 1.353(3) . ?
C4 C9 1.411(3) . ?
C4 C5 1.412(3) . ?
C16 C21 1.385(3) . ?
C16 C17 1.391(3) . ?
C10 C15 1.382(3) . ?
C10 C11 1.387(3) . ?
C2 C1 1.395(3) . ?
C11 C12 1.367(3) . ?
C9 C8 1.400(3) . ?
C23 C24 1.366(3) . ?
C17 C18 1.368(3) . ?
C25 C26 1.371(4) . ?
C25 C24 1.379(4) . ?
C26 C27 1.374(3) . ?
C21 C20 1.371(3) . ?
C6 C5 1.351(3) . ?
C6 C7 1.400(4) . ?
C12 C13 1.359(3) . ?
C13 C14 1.367(4) . ?
C15 C14 1.366(4) . ?
C8 C7 1.356(4) . ?
C18 C19 1.368(4) . ?
C19 C20 1.368(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
O1 P1 C22 112.31(10) . . ?
O1 P1 C16 109.62(9) . . ?
C22 P1 C16 108.48(10) . . ?
O1 P1 C2 112.14(9) . . ?
C22 P1 C2 106.33(9) . . ?
C16 P1 C2 107.77(9) . . ?
C1 N1 C9 117.55(18) . . ?
C27 C22 C23 119.7(2) . . ?
C27 C22 P1 117.93(16) . . ?
C23 C22 P1 122.25(16) . . ?
C2 C3 C4 117.97(19) . . ?
C2 C3 C10 122.98(18) . . ?
C4 C3 C10 119.01(18) . . ?
C9 C4 C5 118.6(2) . . ?
C9 C4 C3 118.59(19) . . ?
C5 C4 C3 122.8(2) . . ?
C21 C16 C17 118.4(2) . . ?
C21 C16 P1 116.85(16) . . ?
C17 C16 P1 124.72(17) . . ?
C15 C10 C11 119.1(2) . . ?
C15 C10 C3 121.95(18) . . ?
C11 C10 C3 118.91(18) . . ?
C3 C2 C1 118.45(18) . . ?
C3 C2 P1 119.97(15) . . ?
C1 C2 P1 121.36(15) . . ?
C12 C11 C10 120.6(2) . . ?
N1 C9 C8 118.7(2) . . ?
N1 C9 C4 122.14(19) . . ?
C8 C9 C4 119.1(2) . . ?
N1 C1 C2 125.22(19) . . ?
C24 C23 C22 120.2(2) . . ?
C18 C17 C16 120.4(2) . . ?
C26 C25 C24 120.4(2) . . ?
C25 C26 C27 119.9(2) . . ?
C26 C27 C22 119.9(2) . . ?
C20 C21 C16 120.6(2) . . ?
C5 C6 C7 119.9(2) . . ?
C13 C12 C11 118.3(2) . . ?
C6 C5 C4 121.0(2) . . ?
F5 C13 C12 118.5(2) . . ?
F5 C13 C14 118.5(2) . . ?
C12 C13 C14 123.0(2) . . ?
C14 C15 C10 120.5(2) . . ?
C7 C8 C9 120.5(2) . . ?
C17 C18 C19 120.4(2) . . ?
C23 C24 C25 119.7(2) . . ?
C8 C7 C6 120.8(2) . . ?
C18 C19 C20 120.0(2) . . ?
C19 C20 C21 120.1(2) . . ?
C15 C14 C13 118.4(2) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.644
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.071
# 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 0.500 0.000 0.500 124 37 ' '
2 1.000 0.500 1.000 124 37 ' '
_platon_squeeze_details          ?
