# 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_i
_database_code_depnum_ccdc_archive 'CCDC 1058977'
_audit_update_record             
;
2015-04-10 deposited with the CCDC.
2016-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H23 B F3 O2 P'
_chemical_formula_sum            'C15 H23 B F3 O2 P'
_chemical_formula_weight         334.11

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'
B B 0.0013 0.0007 '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'

_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                   8.174(8)
_cell_length_b                   14.540(13)
_cell_length_c                   13.759(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.568(12)
_cell_angle_gamma                90.00
_cell_volume                     1634(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       single
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.358
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_absorpt_coefficient_mu    0.202
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9510
_exptl_absorpt_correction_T_max  0.9605
_exptl_absorpt_process_details   ?

_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14009
_diffrn_reflns_av_R_equivalents  0.0576
_diffrn_reflns_av_sigmaI/netI    0.0646
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         28.26
_reflns_number_total             3926
_reflns_number_gt                2715
_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)+(0.0520P)²+0.4336P] 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         3926
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1228
_refine_ls_wR_factor_gt          0.1087
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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 0.24600(6) 0.80737(4) 0.13324(4) 0.01769(15) Uani 1 1 d . . .
F1 F -0.12107(15) 0.81155(10) 0.16359(10) 0.0353(4) Uani 1 1 d . . .
O1 O -0.12845(18) 0.58227(11) 0.14229(11) 0.0264(4) Uani 1 1 d . . .
C1 C 0.0755(2) 0.88954(14) 0.28573(15) 0.0191(5) Uani 1 1 d . . .
B1 B -0.1071(3) 0.87896(18) 0.23557(19) 0.0237(6) Uani 1 1 d . . .
F2 F -0.22103(15) 0.85984(10) 0.30581(10) 0.0361(4) Uani 1 1 d . . .
O2 O -0.06826(18) 0.55570(11) 0.29975(11) 0.0273(4) Uani 1 1 d . . .
H5A H -0.1533 0.5258 0.2959 0.041 Uiso 1 1 calc R . .
C2 C 0.0809(3) 0.93534(15) 0.37497(16) 0.0246(5) Uani 1 1 d . . .
H9A H -0.0164 0.9579 0.3982 0.030 Uiso 1 1 calc R . .
F3 F -0.15513(15) 0.96355(10) 0.19043(10) 0.0333(4) Uani 1 1 d . . .
C3 C 0.2252(3) 0.94879(16) 0.43071(16) 0.0263(5) Uani 1 1 d . . .
H19A H 0.2229 0.9790 0.4902 0.032 Uiso 1 1 calc R . .
C4 C 0.3709(3) 0.91733(15) 0.39761(16) 0.0232(5) Uani 1 1 d . . .
H10A H 0.4674 0.9250 0.4352 0.028 Uiso 1 1 calc R . .
C5 C 0.3735(2) 0.87426(14) 0.30831(15) 0.0206(5) Uani 1 1 d . . .
H13A H 0.4727 0.8545 0.2852 0.025 Uiso 1 1 calc R . .
C6 C 0.2280(2) 0.85983(14) 0.25163(15) 0.0173(4) Uani 1 1 d . . .
C7 C 0.1581(3) 0.88843(15) 0.04437(15) 0.0220(5) Uani 1 1 d . . .
H12A H 0.0564 0.9107 0.0713 0.026 Uiso 1 1 calc R . .
C8 C 0.2684(3) 0.97247(16) 0.03666(17) 0.0284(5) Uani 1 1 d . . .
H14A H 0.2207 1.0145 -0.0104 0.043 Uiso 1 1 calc R . .
H14B H 0.3742 0.9535 0.0167 0.043 Uiso 1 1 calc R . .
H14C H 0.2797 1.0023 0.0989 0.043 Uiso 1 1 calc R . .
C9 C 0.1088(3) 0.84619(17) -0.05475(17) 0.0299(6) Uani 1 1 d . . .
H20A H 0.0636 0.8931 -0.0971 0.045 Uiso 1 1 calc R . .
H20B H 0.0284 0.7991 -0.0464 0.045 Uiso 1 1 calc R . .
H20C H 0.2035 0.8199 -0.0829 0.045 Uiso 1 1 calc R . .
C10 C 0.4618(3) 0.78404(16) 0.11462(16) 0.0236(5) Uani 1 1 d . . .
H15A H 0.5252 0.8380 0.1366 0.028 Uiso 1 1 calc R . .
C11 C 0.5204(3) 0.70149(16) 0.17606(19) 0.0299(6) Uani 1 1 d . . .
H17A H 0.6341 0.6902 0.1658 0.045 Uiso 1 1 calc R . .
H17B H 0.4575 0.6481 0.1572 0.045 Uiso 1 1 calc R . .
H17C H 0.5064 0.7144 0.2436 0.045 Uiso 1 1 calc R . .
C12 C 0.4962(3) 0.76708(19) 0.00707(18) 0.0353(6) Uani 1 1 d . . .
H21A H 0.6110 0.7557 0.0009 0.053 Uiso 1 1 calc R . .
H21B H 0.4644 0.8202 -0.0306 0.053 Uiso 1 1 calc R . .
H21C H 0.4347 0.7147 -0.0163 0.053 Uiso 1 1 calc R . .
C13 C 0.1410(3) 0.69782(15) 0.12185(16) 0.0218(5) Uani 1 1 d . . .
H6A H 0.0349 0.7079 0.0892 0.026 Uiso 1 1 calc R . .
H6B H 0.2032 0.6580 0.0806 0.026 Uiso 1 1 calc R . .
C14 C 0.1153(3) 0.64790(16) 0.21773(16) 0.0243(5) Uani 1 1 d . . .
H16A H 0.2075 0.6074 0.2323 0.029 Uiso 1 1 calc R . .
H16B H 0.1109 0.6926 0.2699 0.029 Uiso 1 1 calc R . .
C15 C -0.0403(2) 0.59247(15) 0.21311(16) 0.0201(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
P1 C6 1.811(3) . ?
P1 C13 1.813(3) . ?
P1 C7 1.823(2) . ?
P1 C10 1.826(3) . ?
F1 B1 1.395(3) . ?
O1 C15 1.195(3) . ?
C1 C2 1.396(3) . ?
C1 C6 1.419(3) . ?
C1 B1 1.623(3) . ?
B1 F2 1.400(3) . ?
B1 F3 1.425(3) . ?
O2 C15 1.336(3) . ?
C2 C3 1.392(3) . ?
C3 C4 1.373(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.408(3) . ?
C7 C8 1.525(3) . ?
C7 C9 1.533(3) . ?
C10 C11 1.532(3) . ?
C10 C12 1.538(4) . ?
C13 C14 1.529(3) . ?
C14 C15 1.505(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
C6 P1 C13 113.00(10) . . ?
C6 P1 C7 106.59(12) . . ?
C13 P1 C7 109.83(11) . . ?
C6 P1 C10 108.83(10) . . ?
C13 P1 C10 106.34(11) . . ?
C7 P1 C10 112.36(11) . . ?
C2 C1 C6 116.29(19) . . ?
C2 C1 B1 114.29(18) . . ?
C6 C1 B1 129.4(2) . . ?
F1 B1 F2 108.3(2) . . ?
F1 B1 F3 106.5(2) . . ?
F2 B1 F3 107.05(18) . . ?
F1 B1 C1 114.41(18) . . ?
F2 B1 C1 110.7(2) . . ?
F3 B1 C1 109.50(19) . . ?
C3 C2 C1 123.0(2) . . ?
C4 C3 C2 119.8(2) . . ?
C3 C4 C5 119.6(2) . . ?
C4 C5 C6 120.9(2) . . ?
C5 C6 C1 120.3(2) . . ?
C5 C6 P1 117.39(15) . . ?
C1 C6 P1 122.28(16) . . ?
C8 C7 C9 113.07(19) . . ?
C8 C7 P1 110.37(15) . . ?
C9 C7 P1 114.69(17) . . ?
C11 C10 C12 109.8(2) . . ?
C11 C10 P1 110.38(15) . . ?
C12 C10 P1 112.59(16) . . ?
C14 C13 P1 115.18(15) . . ?
C15 C14 C13 111.50(18) . . ?
O1 C15 O2 123.8(2) . . ?
O1 C15 C14 125.4(2) . . ?
O2 C15 C14 110.79(18) . . ?

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        28.26
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.361
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.067
