# Electronic Supplementary Material (ESI) for ChemComm.
# 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_1-H2O
_database_code_depnum_ccdc_archive 'CCDC 1445429'
_audit_update_record             
;
2016-01-05 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6.20 N6 O0.10'
_chemical_formula_weight         200.00

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'

_space_group_crystal_system      trigonal
_space_group_IT_number           166
_space_group_name_H-M_alt        'R -3 m :H'
_space_group_name_Hall           '-R 3 2"'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'y, x, -z'
'x-y, -y, -z'
'-x, -x+y, -z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'y+2/3, x+1/3, -z+1/3'
'x-y+2/3, -y+1/3, -z+1/3'
'-x+2/3, -x+y+1/3, -z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'y+1/3, x+2/3, -z+2/3'
'x-y+1/3, -y+2/3, -z+2/3'
'-x+1/3, -x+y+2/3, -z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'

_cell_length_a                   12.657(4)
_cell_length_b                   12.657(4)
_cell_length_c                   9.296(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1289.6(9)
_cell_formula_units_Z            6
_cell_measurement_temperature    117(2)
_cell_measurement_reflns_used    2091
_cell_measurement_theta_min      3.22
_cell_measurement_theta_max      27.24

_exptl_crystal_description       block
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_F_000             618
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      117(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Riguku R-Axis Spider'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3722
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_av_R_equivalents  0.1148
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.219
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             325
_reflns_number_gt                199
_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-2013 (Sheldrick, 2013)'
_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)+(0.0775P)²]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         325
_refine_ls_number_parameters     31
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1549
_refine_ls_wR_factor_gt          0.1335
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
N1 N 0.7955(2) 0.02736(19) 0.8242(3) 0.0565(8) Uani 1 1 d . . . . .
H1 H 0.711(4) -0.020(5) 0.821(6) 0.068 Uiso 0.5 1 d . U P . .
C1 C 0.85107(16) 0.14893(16) 0.8306(4) 0.0611(11) Uani 1 2 d S T P . .
H1A H 0.8079 0.1921 0.8389 0.073 Uiso 1 2 calc R U P . .
C2 C 0.88884(19) 0.00067(19) 0.8139(2) 0.0508(8) Uani 1 1 d . . . . .
O1W O 0.6667 0.3333 0.8333 0.23(4) Uani 0.2 12 d S T P . .
H1W H 0.6216 0.3784 0.8443 0.281 Uiso 0.0667 2 d R U P . .


_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
N1 C1 1.335(3) . ?
N1 C2 1.385(3) . ?
C1 N1 1.335(3) 22_665 ?
C2 C2 1.398(4) 22_665 ?
C2 C2 1.424(4) 24_545 ?

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
C1 N1 C2 105.2(2) . . ?
N1 C1 N1 114.2(3) . 22_665 ?
N1 C2 C2 107.74(12) . 22_665 ?
N1 C2 C2 132.10(12) . 24_545 ?
C2 C2 C2 119.997(1) 22_665 24_545 ?

_refine_diff_density_max         0.185
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.048

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_2-H2O
_database_code_depnum_ccdc_archive 'CCDC 1445430'
_audit_update_record             
;
2016-01-05 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H17 F9 N6 O7'
_chemical_formula_weight         528.31

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'
O O 0.0492 0.0322 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'

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

_cell_length_a                   12.335(4)
_cell_length_b                   21.047(8)
_cell_length_c                   7.890(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2048.4(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    253(2)
_cell_measurement_reflns_used    1151
_cell_measurement_theta_min      6.7
_cell_measurement_theta_max      68.3

_exptl_crystal_description       needle-like
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_F_000             1072
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    1.706
_shelx_estimated_absorpt_T_min   0.595
_shelx_estimated_absorpt_T_max   0.935
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      253(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Pilatus 300K'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16393
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_theta_min         7.014
_diffrn_reflns_theta_max         68.235
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1848
_reflns_number_gt                1679
_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-2013 (Sheldrick, 2013)'
_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)+(0.0544P)²+2.6925P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1848
_refine_ls_number_parameters     248
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.1292
_refine_ls_wR_factor_gt          0.1247
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.323
_refine_ls_shift/su_max          0.002
_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
N1 N 0.38461(14) 0.60572(9) 0.6503(2) 0.0236(4) Uani 1 1 d . . . . .
H1 H 0.390(4) 0.643(3) 0.677(7) 0.028 Uiso 0.5 1 d . U P . .
N2 N 0.30460(15) 0.51362(9) 0.5825(2) 0.0231(4) Uani 1 1 d . . . . .
H2 H 0.258(5) 0.490(3) 0.552(7) 0.028 Uiso 0.5 1 d . U P . .
N3 N 0.42029(15) 0.37895(8) 0.6813(2) 0.0227(4) Uani 1 1 d . . . . .
H3 H 0.373(5) 0.364(3) 0.636(7) 0.027 Uiso 0.5 1 d . U P . .
C1 C 0.20819(18) 0.61271(11) 0.5021(3) 0.0301(5) Uani 1 1 d . . . . .
C2 C 0.30026(17) 0.57721(10) 0.5788(3) 0.0238(5) Uani 1 1 d . . . . .
C3 C 0.44982(16) 0.55697(9) 0.7072(3) 0.0207(5) Uani 1 1 d . . . . .
C4 C 0.39996(16) 0.49957(9) 0.6644(3) 0.0198(4) Uani 1 1 d . . . . .
C5 C 0.45031(16) 0.44127(9) 0.7075(3) 0.0196(4) Uani 1 1 d . . . . .
C6 C 0.5000 0.27369(15) 0.7500 0.0309(7) Uani 1 2 d S T P . .
C7 C 0.5000 0.34477(14) 0.7500 0.0231(6) Uani 1 2 d S T P . .
F1 F 0.1258(15) 0.6169(12) 0.605(3) 0.078(5) Uani 0.55(5) 1 d . . P A 1
F2 F 0.1703(19) 0.5863(7) 0.368(3) 0.078(3) Uani 0.55(5) 1 d . . P A 1
F3 F 0.2363(10) 0.6712(5) 0.4667(14) 0.050(2) Uani 0.55(5) 1 d . . P A 1
F4 F 0.1169(15) 0.6041(14) 0.585(3) 0.066(5) Uani 0.45(5) 1 d . . P A 2
F5 F 0.1907(10) 0.5927(7) 0.3420(13) 0.046(2) Uani 0.45(5) 1 d . . P A 2
F6 F 0.2277(14) 0.6737(5) 0.494(3) 0.070(4) Uani 0.45(5) 1 d . . P A 2
F7 F 0.5640(7) 0.24965(19) 0.6505(10) 0.0943(17) Uani 0.5 1 d . U P . .
F8 F 0.5229(6) 0.25164(16) 0.9032(6) 0.0727(13) Uani 0.5 1 d . U P . .
F9 F 0.4016(3) 0.25078(17) 0.7253(10) 0.0719(13) Uani 0.5 1 d . U P . .
O1W O 0.3803(2) 0.73572(10) 0.7387(3) 0.0459(5) Uani 1 1 d . . . . .
H1WA H 0.390(5) 0.702(4) 0.681(9) 0.055 Uiso 0.5 1 d . U P . .
H1WB H 0.446(6) 0.744(3) 0.713(9) 0.055 Uiso 0.5 1 d . U P . .
H1WC H 0.359(6) 0.763(4) 0.657(10) 0.055 Uiso 0.5 1 d . U P . .
H1WD H 0.327(6) 0.735(3) 0.810(10) 0.055 Uiso 0.5 1 d . U P . .
O2W O 0.12928(17) 0.43824(11) 0.4860(3) 0.0389(5) Uani 1 1 d . . . . .
H2WA H 0.191(6) 0.456(3) 0.522(8) 0.047 Uiso 0.5 1 d . U P . .
H2WB H 0.145(5) 0.398(4) 0.480(8) 0.047 Uiso 0.5 1 d . U P . .
H2WC H 0.093(5) 0.453(3) 0.391(9) 0.047 Uiso 0.5 1 d . U P . .
H2WD H 0.092(6) 0.444(3) 0.556(10) 0.047 Uiso 0.5 1 d . U P . .
O3W O 0.24015(19) 0.32125(10) 0.5176(3) 0.0402(5) Uani 1 1 d . . . . .
H3WA H 0.297(6) 0.336(3) 0.576(8) 0.048 Uiso 0.5 1 d . U P . .
H3WB H 0.199(6) 0.352(4) 0.492(8) 0.048 Uiso 0.5 1 d . U P . .
H3WC H 0.272(5) 0.299(3) 0.428(9) 0.048 Uiso 0.5 1 d . U P . .
H3WD H 0.204(6) 0.297(3) 0.574(9) 0.048 Uiso 0.5 1 d . U P . .
O4W O 0.0000 0.50354(16) 0.2500 0.0382(6) Uani 1 2 d S T P . .
H4WA H 0.040(6) 0.483(3) 0.299(9) 0.046 Uiso 0.5 1 d . U P . .
H4WB H -0.037(5) 0.531(3) 0.317(8) 0.046 Uiso 0.5 1 d . U P . .


_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
N1 C2 1.327(3) . ?
N1 C3 1.379(3) . ?
N1 H1 0.81(6) . ?
N2 C2 1.340(3) . ?
N2 C4 1.374(3) . ?
N2 H2 0.80(7) . ?
N3 C7 1.333(2) . ?
N3 C5 1.378(3) . ?
N3 H3 0.75(6) . ?
C1 F2 1.285(11) . ?
C1 F1 1.302(19) . ?
C1 F6 1.307(11) . ?
C1 F3 1.309(9) . ?
C1 F4 1.316(19) . ?
C1 F5 1.349(12) . ?
C1 C2 1.488(3) . ?
C3 C4 1.397(3) . ?
C3 C3 1.410(4) 3_656 ?
C4 C5 1.417(3) . ?
C5 C5 1.397(4) 3_656 ?
C6 F7 1.223(4) 3_656 ?
C6 F7 1.223(4) . ?
C6 F9 1.321(4) 3_656 ?
C6 F9 1.321(4) . ?
C6 F8 1.325(4) 3_656 ?
C6 F8 1.325(4) . ?
C6 C7 1.496(4) . ?
C7 N3 1.333(2) 3_656 ?
F7 F9 1.068(8) 3_656 ?
F7 F8 1.153(8) 3_656 ?
F8 F7 1.153(8) 3_656 ?
F8 F9 1.377(7) 3_656 ?
F9 F7 1.068(8) 3_656 ?
F9 F8 1.377(7) 3_656 ?
O1W H1WA 0.85(8) . ?
O1W H1WB 0.85(7) . ?
O1W H1WC 0.90(8) . ?
O1W H1WD 0.86(8) . ?
O2W H2WA 0.89(8) . ?
O2W H2WB 0.87(8) . ?
O2W H2WC 0.93(8) . ?
O2W H2WD 0.73(8) . ?
O3W H3WA 0.90(8) . ?
O3W H3WB 0.84(9) . ?
O3W H3WC 0.94(8) . ?
O3W H3WD 0.81(8) . ?
O4W H4WA 0.75(7) . ?
O4W H4WB 0.90(7) . ?

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
C2 N1 C3 105.03(17) . . ?
C2 N1 H1 128(4) . . ?
C3 N1 H1 125(4) . . ?
C2 N2 C4 105.04(18) . . ?
C2 N2 H2 126(4) . . ?
C4 N2 H2 129(4) . . ?
C7 N3 C5 104.74(19) . . ?
C7 N3 H3 122(4) . . ?
C5 N3 H3 133(4) . . ?
F2 C1 F1 104.9(12) . . ?
F2 C1 F3 109.1(10) . . ?
F1 C1 F3 106.0(11) . . ?
F6 C1 F4 108.6(13) . . ?
F6 C1 F5 106.7(10) . . ?
F4 C1 F5 106.7(13) . . ?
F2 C1 C2 113.4(6) . . ?
F1 C1 C2 112.1(8) . . ?
F6 C1 C2 111.9(6) . . ?
F3 C1 C2 110.9(5) . . ?
F4 C1 C2 112.3(8) . . ?
F5 C1 C2 110.3(6) . . ?
N1 C2 N2 114.27(18) . . ?
N1 C2 C1 122.99(19) . . ?
N2 C2 C1 122.74(19) . . ?
N1 C3 C4 107.95(18) . . ?
N1 C3 C3 131.92(11) . 3_656 ?
C4 C3 C3 120.14(12) . 3_656 ?
N2 C4 C3 107.72(17) . . ?
N2 C4 C5 132.40(19) . . ?
C3 C4 C5 119.88(19) . . ?
N3 C5 C5 107.92(11) . 3_656 ?
N3 C5 C4 132.11(19) . . ?
C5 C5 C4 119.98(12) 3_656 . ?
F7 C6 F7 131.1(5) 3_656 . ?
F7 C6 F9 110.4(4) 3_656 3_656 ?
F7 C6 F9 49.5(4) . 3_656 ?
F7 C6 F9 49.5(4) 3_656 . ?
F7 C6 F9 110.4(4) . . ?
F9 C6 F9 137.2(4) 3_656 . ?
F7 C6 F8 107.7(4) 3_656 3_656 ?
F7 C6 F8 53.6(4) . 3_656 ?
F9 C6 F8 101.7(3) 3_656 3_656 ?
F9 C6 F8 62.7(3) . 3_656 ?
F7 C6 F8 53.6(4) 3_656 . ?
F7 C6 F8 107.6(4) . . ?
F9 C6 F8 62.7(3) 3_656 . ?
F9 C6 F8 101.7(3) . . ?
F8 C6 F8 139.0(4) 3_656 . ?
F7 C6 C7 114.4(2) 3_656 . ?
F7 C6 C7 114.4(2) . . ?
F9 C6 C7 111.4(2) 3_656 . ?
F9 C6 C7 111.4(2) . . ?
F8 C6 C7 110.5(2) 3_656 . ?
F8 C6 C7 110.5(2) . . ?
N3 C7 N3 114.7(3) 3_656 . ?
N3 C7 C6 122.65(13) 3_656 . ?
N3 C7 C6 122.65(13) . . ?
F9 F7 F8 134.8(5) 3_656 3_656 ?
F9 F7 C6 70.0(4) 3_656 . ?
F8 F7 C6 67.7(3) 3_656 . ?
F7 F8 C6 58.7(3) 3_656 . ?
F7 F8 F9 111.0(4) 3_656 3_656 ?
C6 F8 F9 58.5(2) . 3_656 ?
F7 F9 C6 60.5(3) 3_656 . ?
F7 F9 F8 114.0(4) 3_656 3_656 ?
C6 F9 F8 58.8(3) . 3_656 ?
H1WA O1W H1WB 85(6) . . ?
H1WA O1W H1WC 100(6) . . ?
H1WB O1W H1WC 89(6) . . ?
H1WA O1W H1WD 117(7) . . ?
H1WB O1W H1WD 151(7) . . ?
H1WC O1W H1WD 105(6) . . ?
H2WA O2W H2WB 103(6) . . ?
H2WA O2W H2WC 122(6) . . ?
H2WB O2W H2WC 113(6) . . ?
H2WA O2W H2WD 102(7) . . ?
H2WB O2W H2WD 111(7) . . ?
H2WC O2W H2WD 105(7) . . ?
H3WA O3W H3WB 109(6) . . ?
H3WA O3W H3WC 103(6) . . ?
H3WB O3W H3WC 117(6) . . ?
H3WA O3W H3WD 111(6) . . ?
H3WB O3W H3WD 106(7) . . ?
H3WC O3W H3WD 110(6) . . ?
H4WA O4W H4WB 113(7) . . ?

_refine_diff_density_max         0.548
_refine_diff_density_min         -0.534
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-2



####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1445431'
_audit_update_record             
;
2016-01-05 deposited with the CCDC.
2016-02-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H3.50 F10.50 N7'
_chemical_formula_weight         469.24

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'

_space_group_crystal_system      cubic
_space_group_IT_number           213
_space_group_name_H-M_alt        'P 41 3 2'
_space_group_name_Hall           'P 4bd 2ab 3'

_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'
'-y+1/4, x+3/4, z+1/4'
'-x+1/2, -y, z+1/2'
'y+1/4, -x+1/4, z+3/4'
'x+1/4, -z+1/4, y+3/4'
'x+1/2, -y+1/2, -z'
'x+3/4, z+1/4, -y+1/4'
'z+3/4, y+1/4, -x+1/4'
'-x, y+1/2, -z+1/2'
'-z+1/4, y+3/4, x+1/4'
'z, x, y'
'y, z, x'
'-y+1/2, -z, x+1/2'
'z+1/2, -x+1/2, -y'
'-y, z+1/2, -x+1/2'
'-z+1/2, -x, y+1/2'
'-z, x+1/2, -y+1/2'
'y+1/2, -z+1/2, -x'
'y+3/4, x+1/4, -z+1/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x+1/4, z+3/4, y+1/4'
'-x+3/4, -z+3/4, -y+3/4'
'z+1/4, -y+1/4, x+3/4'
'-z+3/4, -y+3/4, -x+3/4'

_cell_length_a                   15.8427(15)
_cell_length_b                   15.8427(15)
_cell_length_c                   15.8427(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3976.4(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4036
_cell_measurement_theta_min      32.4
_cell_measurement_theta_max      68.2

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_F_000             1848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.549
_shelx_estimated_absorpt_T_min   0.654
_shelx_estimated_absorpt_T_max   0.747
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'XtaLAB P300DS'
_diffrn_measurement_method       '/w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25149
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         6.845
_diffrn_reflns_theta_max         68.377
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1226
_reflns_number_gt                1211
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.578
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    0.998

_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-2013 (Sheldrick, 2013)'
_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)+(0.0750P)²+9.9836P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0026(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 444 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.02(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1226
_refine_ls_number_parameters     155
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0801
_refine_ls_R_factor_gt           0.0797
_refine_ls_wR_factor_ref         0.2114
_refine_ls_wR_factor_gt          0.2113
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.190
_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
N1 N 0.6230(3) 0.1217(3) -0.0056(3) 0.0419(12) Uani 1 1 d . . . . .
H1 H 0.668(4) 0.130(4) -0.036(4) 0.041(17) Uiso 1 1 d . . . . .
N2 N 0.5301(3) 0.1414(3) 0.0999(3) 0.0452(13) Uani 1 1 d . . . . .
F1A F 0.6174(18) 0.2804(19) 0.1562(15) 0.074(6) Uani 0.39(3) 1 d . U P A 2
F1 F 0.7094(10) 0.2159(8) 0.1485(14) 0.104(6) Uani 0.61(3) 1 d . U P A 1
F2A F 0.6482(19) 0.3006(14) 0.0228(16) 0.094(7) Uani 0.39(3) 1 d . U P A 2
F2 F 0.6898(14) 0.2792(12) 0.0347(10) 0.100(6) Uani 0.61(3) 1 d . U P A 1
F3A F 0.7274(11) 0.2281(13) 0.097(2) 0.100(8) Uani 0.39(3) 1 d . U P A 2
F3 F 0.5981(12) 0.2950(12) 0.1318(14) 0.090(5) Uani 0.61(3) 1 d . U P A 1
C1 C 0.6498(5) 0.2422(5) 0.0913(6) 0.071(2) Uani 1 1 d . . . . .
C2 C 0.5997(4) 0.1681(4) 0.0627(4) 0.0446(15) Uani 1 1 d . . . . .
C3 C 0.5631(4) 0.0590(3) -0.0135(3) 0.0362(13) Uani 1 1 d . . . . .
C4 C 0.5075(3) 0.0716(3) 0.0526(4) 0.0361(13) Uani 1 1 d . . . . .
N3 N 0.6845(15) 0.0110(15) 0.2083(15) 0.136(6) Uani 0.3333 1 d D U P . .
H3 H 0.7297 0.0427 0.2027 0.163 Uiso 0.1667 1 calc R U P . .
C5 C 0.6599(11) -0.0544(11) 0.1597(11) 0.111(7) Uani 0.3333 1 d D U P . .
C6 C 0.6250 0.0163(12) 0.2663(12) 0.161(7) Uani 0.3333 2 d DS TU P . .
C7 C 0.6250 0.0812(17) 0.3312(17) 0.189(7) Uani 0.3333 2 d DS TU P . .
F4 F 0.586(3) 0.145(3) 0.286(3) 0.198(8) Uani 0.25 1 d . U P . .
F5 F 0.6664(11) 0.1664(11) 0.3336(11) 0.207(7) Uani 0.75 3 d S TU P . .


_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
N1 C2 1.359(8) . ?
N1 C3 1.380(7) . ?
N1 H1 0.87(7) . ?
N2 C2 1.321(8) . ?
N2 C4 1.383(7) . ?
F1A C1 1.30(3) . ?
F1 C1 1.373(16) . ?
F2A C1 1.43(3) . ?
F2 C1 1.245(15) . ?
F3A C1 1.25(2) . ?
F3 C1 1.34(2) . ?
C1 C2 1.488(9) . ?
C3 C4 1.383(8) . ?
C3 C4 1.410(7) 14 ?
C4 C3 1.410(7) 13_554 ?
N3 C6 1.318(13) . ?
N3 C5 1.348(13) . ?
N3 H3 0.8800 . ?
C5 C5 1.362(14) 19_545 ?
C5 C5 1.366(14) 21_645 ?
C6 N3 1.318(13) 21_645 ?
C6 C7 1.46(3) . ?
C7 F4 1.39(5) . ?
C7 F4 1.39(5) 21_645 ?
C7 F4 1.46(5) 17_645 ?
C7 F4 1.46(5) 23_554 ?
C7 F5 1.50(3) . ?
C7 F5 1.50(3) 20 ?
C7 C7 1.70(7) 17_645 ?
C7 C7 1.70(7) 18_556 ?
F4 F4 1.29(9) 23_554 ?
F4 C7 1.46(5) 18_556 ?
F4 F5 1.52(5) . ?
F5 C7 1.50(3) 17_645 ?
F5 C7 1.50(3) 18_556 ?
F5 F4 1.52(5) 18_556 ?
F5 F4 1.52(5) 17_645 ?

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
C2 N1 C3 105.9(5) . . ?
C2 N1 H1 126(4) . . ?
C3 N1 H1 128(4) . . ?
C2 N2 C4 103.3(5) . . ?
F3A C1 F1A 114.8(17) . . ?
F2 C1 F3 111.3(13) . . ?
F2 C1 F1 105.6(11) . . ?
F3 C1 F1 107.1(11) . . ?
F3A C1 F2A 100.6(14) . . ?
F1A C1 F2A 107.0(16) . . ?
F2 C1 C2 115.0(9) . . ?
F3A C1 C2 113.8(11) . . ?
F1A C1 C2 113.4(13) . . ?
F3 C1 C2 108.2(10) . . ?
F1 C1 C2 109.2(8) . . ?
F2A C1 C2 105.6(11) . . ?
N2 C2 N1 114.2(5) . . ?
N2 C2 C1 124.2(6) . . ?
N1 C2 C1 121.6(6) . . ?
N1 C3 C4 105.4(5) . . ?
N1 C3 C4 132.7(5) . 14 ?
C4 C3 C4 121.9(6) . 14 ?
N2 C4 C3 111.2(5) . . ?
N2 C4 C3 130.7(5) . 13_554 ?
C3 C4 C3 118.1(5) . 13_554 ?
C6 N3 C5 104(2) . . ?
C6 N3 H3 128.1 . . ?
C5 N3 H3 128.1 . . ?
C5 C5 C5 119.98(11) 19_545 21_645 ?
C5 C5 N3 131.4(9) 19_545 . ?
C5 C5 N3 108.4(9) 21_645 . ?
N3 C6 N3 115(3) . 21_645 ?
N3 C6 C7 122.5(13) . . ?
N3 C6 C7 122.5(13) 21_645 . ?
F4 C7 F4 162(5) . 21_645 ?
F4 C7 C6 99(3) . . ?
F4 C7 C6 99(3) 21_645 . ?
F4 C7 F4 122(4) . 17_645 ?
F4 C7 F4 54(3) 21_645 17_645 ?
C6 C7 F4 102(3) . 17_645 ?
F4 C7 F4 54(3) . 23_554 ?
F4 C7 F4 122(4) 21_645 23_554 ?
C6 C7 F4 102(3) . 23_554 ?
F4 C7 F4 155(5) 17_645 23_554 ?
F4 C7 F5 63(2) . . ?
F4 C7 F5 104(3) 21_645 . ?
C6 C7 F5 130.8(14) . . ?
F4 C7 F5 62(2) 17_645 . ?
F4 C7 F5 101(3) 23_554 . ?
F4 C7 F5 104(3) . 20 ?
F4 C7 F5 63(2) 21_645 20 ?
C6 C7 F5 130.8(14) . 20 ?
F4 C7 F5 101(3) 17_645 20 ?
F4 C7 F5 62(2) 23_554 20 ?
F5 C7 F5 98(3) . 20 ?
F4 C7 C7 108(3) . 17_645 ?
F4 C7 C7 55(3) 21_645 17_645 ?
C6 C7 C7 150.001(3) . 17_645 ?
F4 C7 C7 52(2) 17_645 17_645 ?
F4 C7 C7 104(2) 23_554 17_645 ?
F5 C7 C7 55.5(11) . 17_645 ?
F5 C7 C7 55.5(11) 20 17_645 ?
F4 C7 C7 55(3) . 18_556 ?
F4 C7 C7 108(3) 21_645 18_556 ?
C6 C7 C7 150.001(4) . 18_556 ?
F4 C7 C7 104(2) 17_645 18_556 ?
F4 C7 C7 52(2) 23_554 18_556 ?
F5 C7 C7 55.5(11) . 18_556 ?
F5 C7 C7 55.5(11) 20 18_556 ?
C7 C7 C7 59.999(1) 17_645 18_556 ?
F4 F4 C7 66(3) 23_554 . ?
F4 F4 C7 60(3) 23_554 18_556 ?
C7 F4 C7 73(4) . 18_556 ?
F4 F4 F5 109(2) 23_554 . ?
C7 F4 F5 62(3) . . ?
C7 F4 F5 61(2) 18_556 . ?
C7 F5 C7 69(2) 17_645 18_556 ?
C7 F5 C7 69(2) 17_645 . ?
C7 F5 C7 69(2) 18_556 . ?
C7 F5 F4 112(3) 17_645 . ?
C7 F5 F4 57.7(18) 18_556 . ?
C7 F5 F4 54.7(19) . . ?
C7 F5 F4 57.7(18) 17_645 18_556 ?
C7 F5 F4 54.7(19) 18_556 18_556 ?
C7 F5 F4 112(3) . 18_556 ?
F4 F5 F4 109.9(19) . 18_556 ?
C7 F5 F4 54.7(19) 17_645 17_645 ?
C7 F5 F4 112(3) 18_556 17_645 ?
C7 F5 F4 57.7(18) . 17_645 ?
F4 F5 F4 109.9(19) . 17_645 ?
F4 F5 F4 109.9(19) 18_556 17_645 ?

_refine_diff_density_max         0.791
_refine_diff_density_min         -0.828
_refine_diff_density_rms         0.106

_shelxl_version_number           2013-2



