# Electronic Supplementary Material (ESI) for Analytical Methods.
# 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_PP_BU02_a
_database_code_depnum_ccdc_archive 'CCDC 1500636'
_audit_update_record             
;
2016-08-23 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H4 F10 N4 O'
_chemical_formula_weight         422.20

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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.6959(10)
_cell_length_b                   7.2819(6)
_cell_length_c                   13.7456(10)
_cell_angle_alpha                90
_cell_angle_beta                 94.301(5)
_cell_angle_gamma                90
_cell_volume                     1466.83(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.212
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22742
_diffrn_reflns_av_unetI/netI     0.0400
_diffrn_reflns_av_R_equivalents  0.0598
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.390
_diffrn_reflns_theta_max         26.618
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3056
_reflns_number_gt                1752
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1077P)²+0.3645P] 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         3056
_refine_ls_number_parameters     253
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.1965
_refine_ls_wR_factor_gt          0.1594
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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
O001 O 0.53011(13) 0.9830(3) 0.38987(14) 0.0422(5) Uani 1 1 d . . . . .
F002 F 0.30546(13) 0.7932(3) 0.43766(14) 0.0646(6) Uani 1 1 d . . . . .
F003 F 0.26567(13) 0.5181(3) 0.12757(14) 0.0701(7) Uani 1 1 d . . . . .
F004 F 0.66900(15) 0.8438(3) 0.66571(16) 0.0768(7) Uani 1 1 d . . . . .
F005 F 0.65912(16) 0.5112(4) 0.37103(16) 0.0893(8) Uani 1 1 d . . . . .
N006 N 0.38611(15) 0.6433(3) 0.27577(17) 0.0404(6) Uani 1 1 d . . . . .
H006 H 0.4122 0.5410 0.2633 0.048 Uiso 1 1 calc R U . . .
F007 F 0.12382(16) 0.8066(4) 0.44544(18) 0.0924(8) Uani 1 1 d . . . . .
N008 N 0.43548(16) 0.8072(3) 0.29201(17) 0.0416(6) Uani 1 1 d . . . . .
H008 H 0.4289 0.8939 0.2496 0.050 Uiso 1 1 calc R U . . .
F009 F 0.08347(15) 0.5241(4) 0.13817(17) 0.0897(8) Uani 1 1 d . . . . .
N00A N 0.56125(16) 0.6963(3) 0.51880(17) 0.0417(6) Uani 1 1 d . . . . .
H00A H 0.5361 0.7067 0.5731 0.050 Uiso 1 1 calc R U . . .
F00B F 0.85187(16) 0.8358(3) 0.6745(2) 0.0977(9) Uani 1 1 d . . . . .
F00C F 0.94014(15) 0.6702(4) 0.5305(2) 0.0997(9) Uani 1 1 d . . . . .
N1 N 0.50884(17) 0.6841(3) 0.42961(18) 0.0471(7) Uani 1 1 d . . . . .
H1 H 0.4863 0.5799 0.4109 0.057 Uiso 1 1 calc R U . . .
F00E F 0.01098(14) 0.6707(4) 0.2978(2) 0.0989(9) Uani 1 1 d . . . . .
F00F F 0.83968(18) 0.5084(4) 0.37954(18) 0.1003(9) Uani 1 1 d . . . . .
C00G C 0.49337(18) 0.8325(4) 0.3730(2) 0.0363(7) Uani 1 1 d . . . . .
C00H C 0.29082(19) 0.6580(4) 0.2813(2) 0.0381(7) Uani 1 1 d . . . . .
C00I C 0.6568(2) 0.6910(4) 0.5158(2) 0.0405(7) Uani 1 1 d . . . . .
C00J C 0.2314(2) 0.5891(4) 0.2070(2) 0.0469(8) Uani 1 1 d . . . . .
C00K C 0.2509(2) 0.7299(4) 0.3608(2) 0.0466(8) Uani 1 1 d . . . . .
C00L C 0.7108(2) 0.7651(4) 0.5922(2) 0.0493(8) Uani 1 1 d . . . . .
C00M C 0.7041(2) 0.6014(5) 0.4458(2) 0.0520(8) Uani 1 1 d . . . . .
C00N C 0.1377(2) 0.5915(5) 0.2126(3) 0.0575(9) Uani 1 1 d . . . . .
C00O C 0.8047(2) 0.7606(5) 0.5974(3) 0.0604(10) Uani 1 1 d . . . . .
C00P C 0.7986(3) 0.5972(5) 0.4495(3) 0.0628(10) Uani 1 1 d . . . . .
C00Q C 0.1011(2) 0.6677(5) 0.2917(3) 0.0634(10) Uani 1 1 d . . . . .
C00R C 0.1579(2) 0.7361(5) 0.3658(3) 0.0590(9) Uani 1 1 d . . . . .
C00S C 0.8492(2) 0.6777(5) 0.5252(3) 0.0634(10) 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
O001 C00G 1.235(3) . ?
F002 C00K 1.358(3) . ?
F003 C00J 1.340(4) . ?
F004 C00L 1.349(4) . ?
F005 C00M 1.350(4) . ?
N006 N008 1.406(3) . ?
N006 C00H 1.412(4) . ?
N006 H006 0.8600 . ?
F007 C00R 1.339(4) . ?
N008 C00G 1.362(3) . ?
N008 H008 0.8600 . ?
F009 C00N 1.342(4) . ?
N00A N1 1.401(3) . ?
N00A C00I 1.409(4) . ?
N00A H00A 0.8600 . ?
F00B C00O 1.339(4) . ?
F00C C00S 1.334(4) . ?
N1 C00G 1.341(3) . ?
N1 H1 0.8600 . ?
F00E C00Q 1.333(4) . ?
F00F C00P 1.339(4) . ?
C00H C00K 1.381(4) . ?
C00H C00J 1.387(4) . ?
C00I C00L 1.378(4) . ?
C00I C00M 1.391(4) . ?
C00J C00N 1.384(5) . ?
C00K C00R 1.375(5) . ?
C00L C00O 1.377(5) . ?
C00M C00P 1.386(5) . ?
C00N C00Q 1.367(5) . ?
C00O C00S 1.370(5) . ?
C00P C00S 1.365(5) . ?
C00Q C00R 1.362(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
N008 N006 C00H 115.4(2) . . ?
N008 N006 H006 122.3 . . ?
C00H N006 H006 122.3 . . ?
C00G N008 N006 121.9(2) . . ?
C00G N008 H008 119.1 . . ?
N006 N008 H008 119.1 . . ?
N1 N00A C00I 117.2(2) . . ?
N1 N00A H00A 121.4 . . ?
C00I N00A H00A 121.4 . . ?
C00G N1 N00A 121.0(2) . . ?
C00G N1 H1 119.5 . . ?
N00A N1 H1 119.5 . . ?
O001 C00G N1 123.6(2) . . ?
O001 C00G N008 120.7(2) . . ?
N1 C00G N008 115.7(2) . . ?
C00K C00H C00J 116.0(3) . . ?
C00K C00H N006 123.6(3) . . ?
C00J C00H N006 120.3(3) . . ?
C00L C00I C00M 114.9(3) . . ?
C00L C00I N00A 119.0(3) . . ?
C00M C00I N00A 125.8(3) . . ?
F003 C00J C00H 119.0(3) . . ?
F003 C00J C00N 119.1(3) . . ?
C00H C00J C00N 121.9(3) . . ?
F002 C00K C00R 118.7(3) . . ?
F002 C00K C00H 118.9(3) . . ?
C00R C00K C00H 122.4(3) . . ?
F004 C00L C00I 117.9(3) . . ?
F004 C00L C00O 118.8(3) . . ?
C00I C00L C00O 123.2(3) . . ?
F005 C00M C00P 116.7(3) . . ?
F005 C00M C00I 120.9(3) . . ?
C00P C00M C00I 122.5(3) . . ?
F009 C00N C00Q 120.5(3) . . ?
F009 C00N C00J 119.4(3) . . ?
C00Q C00N C00J 120.1(3) . . ?
F00B C00O C00S 120.5(3) . . ?
F00B C00O C00L 119.3(3) . . ?
C00S C00O C00L 120.2(3) . . ?
F00F C00P C00S 120.4(3) . . ?
F00F C00P C00M 119.3(3) . . ?
C00S C00P C00M 120.3(3) . . ?
F00E C00Q C00R 120.2(3) . . ?
F00E C00Q C00N 120.6(3) . . ?
C00R C00Q C00N 119.2(3) . . ?
F007 C00R C00Q 120.4(3) . . ?
F007 C00R C00K 119.2(3) . . ?
C00Q C00R C00K 120.4(3) . . ?
F00C C00S C00O 120.6(4) . . ?
F00C C00S C00P 120.7(4) . . ?
C00O C00S C00P 118.7(3) . . ?

_refine_diff_density_max         0.491
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.058

_shelxl_version_number           2014/6

