# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_hclo4-revised
_database_code_depnum_ccdc_archive 'CCDC 1857442'
_audit_update_record             
;
2018-07-22 deposited with the CCDC.	2019-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 Cl N5 O8'
_chemical_formula_weight         417.77

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'
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/c

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

_cell_length_a                   12.646(5)
_cell_length_b                   12.620(5)
_cell_length_c                   11.356(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 104.910(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1751.3(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1730
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.584
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    0.276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            23893
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_sigmaI/netI    0.0198
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         24.77
_reflns_number_total             2940
_reflns_number_gt                2559
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'

_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)+(0.0627P)²+0.8450P] 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       0.025(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2940
_refine_ls_number_parameters     281
_refine_ls_number_restraints     480
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.1148
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.012
_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
Cl1 Cl 1.10094(5) 0.28553(5) 0.60083(5) 0.0497(2) Uani 1 1 d U . .
O1 O 0.53750(12) 0.20825(12) 0.27456(12) 0.0419(4) Uani 1 1 d U . .
O2 O 0.42037(11) 0.11723(12) 0.60758(12) 0.0392(4) Uani 1 1 d U . .
N2 N 0.48066(12) 0.16741(12) 0.44379(14) 0.0307(4) Uani 1 1 d U . .
N5 N 0.42547(14) 0.39112(13) 0.36725(15) 0.0363(4) Uani 1 1 d U . .
H5A H 0.4942 0.3790 0.4092 0.054 Uiso 1 1 calc R . .
H5B H 0.4078 0.4579 0.3785 0.054 Uiso 1 1 calc R . .
H5C H 0.4192 0.3800 0.2883 0.054 Uiso 1 1 calc R . .
C7 C 0.66696(15) 0.13707(15) 0.44149(17) 0.0306(4) Uani 1 1 d U . .
C3 C 0.80323(15) 0.06361(15) 0.61986(16) 0.0297(4) Uani 1 1 d U . .
C13 C 0.37000(16) 0.20450(16) 0.38234(19) 0.0354(5) Uani 1 1 d U . .
H13A H 0.3168 0.1605 0.4074 0.042 Uiso 1 1 calc R . .
H13B H 0.3585 0.1963 0.2950 0.042 Uiso 1 1 calc R . .
N1 N 1.00892(14) -0.00307(15) 0.72467(16) 0.0416(4) Uani 1 1 d U . .
H1 H 1.0744 -0.0243 0.7582 0.050 Uiso 1 1 calc R . .
C6 C 0.69055(15) 0.09918(14) 0.56015(16) 0.0288(4) Uani 1 1 d U . .
C9 C 0.49754(15) 0.12572(14) 0.56108(17) 0.0305(4) Uani 1 1 d U . .
C14 C 0.35097(16) 0.31859(16) 0.41011(19) 0.0362(5) Uani 1 1 d U . .
H14A H 0.2758 0.3375 0.3711 0.043 Uiso 1 1 calc R . .
H14B H 0.3621 0.3270 0.4974 0.043 Uiso 1 1 calc R . .
C1 C 0.95218(17) -0.05202(17) 0.62478(19) 0.0393(5) Uani 1 1 d U . .
H1A H 0.9830 -0.1083 0.5925 0.047 Uiso 1 1 calc R . .
C2 C 0.84881(16) -0.01933(16) 0.57003(18) 0.0346(5) Uani 1 1 d U . .
H2 H 0.8089 -0.0525 0.4994 0.041 Uiso 1 1 calc R . .
C4 C 0.86532(17) 0.11218(17) 0.72379(19) 0.0395(5) Uani 1 1 d U . .
H4 H 0.8368 0.1684 0.7588 0.047 Uiso 1 1 calc R . .
C10 C 0.60730(15) 0.09358(15) 0.61941(16) 0.0309(4) Uani 1 1 d U . .
C11 C 0.74780(16) 0.14121(16) 0.37496(17) 0.0344(5) Uani 1 1 d U . .
C5 C 0.96912(18) 0.07666(19) 0.7745(2) 0.0450(5) Uani 1 1 d U . .
H5 H 1.0117 0.1089 0.8443 0.054 Uiso 1 1 calc R . .
C8 C 0.56038(15) 0.17278(15) 0.37916(17) 0.0310(4) Uani 1 1 d U . .
N4 N 0.63766(17) 0.01413(18) 0.83334(18) 0.0560(6) Uani 1 1 d U . .
N3 N 0.81100(15) 0.14284(17) 0.31960(16) 0.0483(5) Uani 1 1 d U . .
C12 C 0.62530(16) 0.05036(17) 0.73811(18) 0.0372(5) Uani 1 1 d U . .
O7 O 0.60555(12) 0.11119(12) 0.08307(13) 0.0442(4) Uani 1 1 d DU . .
H7B H 0.5966 0.1459 0.1428 0.066 Uiso 1 1 d RD . .
H7A H 0.6709 0.1139 0.0816 0.066 Uiso 1 1 d RD . .
O8 O 1.17717(14) -0.07131(19) 0.93983(15) 0.0722(6) Uani 1 1 d DU . .
H8B H 1.1338 -0.1176 0.9513 0.108 Uiso 1 1 d RD . .
H8A H 1.1900 -0.0385 1.0043 0.108 Uiso 1 1 d RD . .
O3 O 0.9897(2) 0.2688(2) 0.5459(3) 0.1120(9) Uani 1 1 d U A .
O4 O 1.1359(5) 0.2773(4) 0.4889(4) 0.0889(16) Uani 0.50 1 d PU A 1
O4A O 1.1765(5) 0.2306(6) 0.5674(8) 0.121(2) Uani 0.50 1 d PU A 2
O5 O 1.1127(6) 0.3985(5) 0.5869(6) 0.103(2) Uani 0.50 1 d PU A 1
O5A O 1.1444(6) 0.3708(6) 0.6630(8) 0.127(3) Uani 0.50 1 d PU A 2
O6 O 1.1066(5) 0.2766(5) 0.7262(4) 0.0996(16) Uani 0.50 1 d PU A 1
O6A O 1.1480(4) 0.1869(4) 0.6585(5) 0.0970(15) Uani 0.50 1 d PU A 2


_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
Cl1 O4A 1.313(5) . ?
Cl1 O5A 1.326(6) . ?
Cl1 O3 1.401(3) . ?
Cl1 O6 1.411(4) . ?
Cl1 O5 1.446(6) . ?
Cl1 O4 1.453(4) . ?
Cl1 O6A 1.460(5) . ?
O1 C8 1.232(2) . ?
O2 C9 1.228(2) . ?
N2 C8 1.393(3) . ?
N2 C9 1.397(2) . ?
N2 C13 1.470(2) . ?
N5 C14 1.483(3) . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
N5 H5C 0.8900 . ?
C7 C6 1.388(3) . ?
C7 C11 1.420(3) . ?
C7 C8 1.425(3) . ?
C3 C4 1.381(3) . ?
C3 C2 1.384(3) . ?
C3 C6 1.481(3) . ?
C13 C14 1.507(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N1 C5 1.316(3) . ?
N1 C1 1.328(3) . ?
N1 H1 0.8600 . ?
C6 C10 1.390(3) . ?
C9 C10 1.434(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C1 C2 1.359(3) . ?
C1 H1A 0.9300 . ?
C2 H2 0.9300 . ?
C4 C5 1.366(3) . ?
C4 H4 0.9300 . ?
C10 C12 1.417(3) . ?
C11 N3 1.137(3) . ?
C5 H5 0.9300 . ?
N4 C12 1.147(3) . ?
O7 H7B 0.8390 . ?
O7 H7A 0.8314 . ?
O8 H8B 0.8339 . ?
O8 H8A 0.8203 . ?
O4A O6A 1.302(9) . ?

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
O4A Cl1 O5A 110.4(4) . . ?
O4A Cl1 O3 120.9(3) . . ?
O5A Cl1 O3 126.2(3) . . ?
O4A Cl1 O6 113.4(5) . . ?
O5A Cl1 O6 67.7(5) . . ?
O3 Cl1 O6 102.8(3) . . ?
O4A Cl1 O5 112.7(5) . . ?
O5A Cl1 O5 38.6(4) . . ?
O3 Cl1 O5 102.7(3) . . ?
O6 Cl1 O5 102.0(4) . . ?
O4A Cl1 O4 45.7(4) . . ?
O5A Cl1 O4 110.2(5) . . ?
O3 Cl1 O4 95.5(3) . . ?
O6 Cl1 O4 158.3(3) . . ?
O5 Cl1 O4 84.9(4) . . ?
O4A Cl1 O6A 55.7(4) . . ?
O5A Cl1 O6A 112.8(5) . . ?
O3 Cl1 O6A 108.6(3) . . ?
O6 Cl1 O6A 64.6(3) . . ?
O5 Cl1 O6A 148.0(4) . . ?
O4 Cl1 O6A 98.7(3) . . ?
C8 N2 C9 124.55(16) . . ?
C8 N2 C13 117.64(16) . . ?
C9 N2 C13 117.77(16) . . ?
C14 N5 H5A 109.5 . . ?
C14 N5 H5B 109.5 . . ?
H5A N5 H5B 109.5 . . ?
C14 N5 H5C 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
C6 C7 C11 121.66(17) . . ?
C6 C7 C8 122.07(17) . . ?
C11 C7 C8 116.27(17) . . ?
C4 C3 C2 118.68(18) . . ?
C4 C3 C6 121.67(17) . . ?
C2 C3 C6 119.65(17) . . ?
N2 C13 C14 112.88(16) . . ?
N2 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N2 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C5 N1 C1 122.70(18) . . ?
C5 N1 H1 118.7 . . ?
C1 N1 H1 118.7 . . ?
C7 C6 C10 119.16(18) . . ?
C7 C6 C3 119.33(16) . . ?
C10 C6 C3 121.49(17) . . ?
O2 C9 N2 119.98(17) . . ?
O2 C9 C10 123.95(18) . . ?
N2 C9 C10 116.06(16) . . ?
N5 C14 C13 111.84(16) . . ?
N5 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
N5 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
N1 C1 C2 119.61(19) . . ?
N1 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
C1 C2 C3 119.68(19) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C5 C4 C3 119.2(2) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C6 C10 C12 121.59(17) . . ?
C6 C10 C9 121.72(17) . . ?
C12 C10 C9 116.59(17) . . ?
N3 C11 C7 178.3(2) . . ?
N1 C5 C4 120.1(2) . . ?
N1 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
O1 C8 N2 120.22(17) . . ?
O1 C8 C7 123.46(17) . . ?
N2 C8 C7 116.31(16) . . ?
N4 C12 C10 178.4(2) . . ?
H7B O7 H7A 109.7 . . ?
H8B O8 H8A 101.6 . . ?
O6A O4A Cl1 67.9(4) . . ?
O4A O6A Cl1 56.4(3) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        24.77
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.443
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.043
####################################################################### 
# 
# 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_hcl-revised
_database_code_depnum_ccdc_archive 'CCDC 1857443'
_audit_update_record             
;
2018-07-22 deposited with the CCDC.	2019-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 Cl N5 O2'
_chemical_formula_weight         317.74

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'
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   C2/c

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

_cell_length_a                   10.873(5)
_cell_length_b                   17.015(5)
_cell_length_c                   15.789(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 93.762(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2914.7(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1390
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18378
_diffrn_reflns_av_R_equivalents  0.0642
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2503
_reflns_number_gt                2202
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'

_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)+(0.0663P)²+1.4042P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2503
_refine_ls_number_parameters     210
_refine_ls_number_restraints     346
_refine_ls_R_factor_all          0.0442
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1032
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      0.972
_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
Cl1 Cl 0.0000 0.20071(3) 0.7500 0.04053(18) Uani 1 2 d SU . .
Cl2 Cl 0.0000 0.0000 0.5000 0.066(2) Uani 0.40 2 d SPU A 1
Cl2A Cl 0.0151(8) -0.0071(6) 0.5338(4) 0.0613(14) Uani 0.30 1 d PU . 2
O1 O 0.41551(11) 0.13176(7) 0.41314(7) 0.0445(3) Uani 1 1 d U . .
O2 O 0.39047(11) 0.29820(6) 0.63547(8) 0.0451(3) Uani 1 1 d U . .
N2 N 0.40118(11) 0.21404(7) 0.52541(8) 0.0326(3) Uani 1 1 d U . .
C6 C 0.33558(12) 0.08917(8) 0.62618(9) 0.0297(3) Uani 1 1 d U . .
N1 N 0.22701(13) -0.10309(8) 0.77082(9) 0.0442(4) Uani 1 1 d U . .
H1 H 0.2024 -0.1431 0.7983 0.053 Uiso 1 1 calc R . .
C7 C 0.35587(13) 0.07711(9) 0.54127(10) 0.0330(3) Uani 1 1 d U . .
N5 N 0.61525(12) 0.35248(8) 0.42618(8) 0.0375(3) Uani 1 1 d U . .
H5A H 0.5855 0.3449 0.3729 0.056 Uiso 1 1 calc R . .
H5B H 0.6971 0.3555 0.4276 0.056 Uiso 1 1 calc R . .
H5C H 0.5851 0.3970 0.4458 0.056 Uiso 1 1 calc R . .
C13 C 0.43962(14) 0.27947(9) 0.47320(11) 0.0355(4) Uani 1 1 d U . .
H13A H 0.4038 0.3280 0.4923 0.043 Uiso 1 1 calc R . .
H13B H 0.4105 0.2710 0.4145 0.043 Uiso 1 1 calc R . .
N4 N 0.32768(14) 0.20002(9) 0.81712(10) 0.0488(4) Uani 1 1 d U . .
C11 C 0.34320(13) 0.00254(10) 0.50090(10) 0.0365(4) Uani 1 1 d U . .
N3 N 0.33650(14) -0.05738(10) 0.46794(11) 0.0530(4) Uani 1 1 d U . .
C5 C 0.16497(16) -0.03585(10) 0.77484(12) 0.0442(4) Uani 1 1 d U . .
H5 H 0.0988 -0.0321 0.8091 0.053 Uiso 1 1 calc R . .
C4 C 0.19879(15) 0.02777(9) 0.72851(11) 0.0388(4) Uani 1 1 d U . .
H4 H 0.1545 0.0745 0.7300 0.047 Uiso 1 1 calc R . .
C10 C 0.34748(13) 0.16458(9) 0.66053(9) 0.0313(3) Uani 1 1 d U . .
C3 C 0.29952(13) 0.02193(8) 0.67947(10) 0.0318(3) Uani 1 1 d U . .
C9 C 0.38015(13) 0.22969(9) 0.60937(10) 0.0323(3) Uani 1 1 d U . .
C12 C 0.33577(13) 0.18234(9) 0.74764(10) 0.0345(4) Uani 1 1 d U . .
C1 C 0.32525(17) -0.11063(10) 0.72608(12) 0.0456(4) Uani 1 1 d U . .
H1A H 0.3674 -0.1582 0.7260 0.055 Uiso 1 1 calc R . .
C14 C 0.57880(15) 0.28604(10) 0.47958(11) 0.0399(4) Uani 1 1 d U . .
H14A H 0.6083 0.2949 0.5381 0.048 Uiso 1 1 calc R . .
H14B H 0.6150 0.2376 0.4603 0.048 Uiso 1 1 calc R . .
C2 C 0.36465(15) -0.04834(9) 0.67998(11) 0.0390(4) Uani 1 1 d U . .
H2 H 0.4344 -0.0531 0.6493 0.047 Uiso 1 1 calc R . .
C8 C 0.39286(13) 0.13998(9) 0.48768(10) 0.0327(3) Uani 1 1 d U . .


_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
Cl2A Cl2A 1.121(12) 5_556 ?
O1 C8 1.2261(19) . ?
O2 C9 1.2391(19) . ?
N2 C9 1.386(2) . ?
N2 C8 1.394(2) . ?
N2 C13 1.4625(19) . ?
C6 C7 1.388(2) . ?
C6 C10 1.396(2) . ?
C6 C3 1.488(2) . ?
N1 C1 1.325(2) . ?
N1 C5 1.332(2) . ?
N1 H1 0.8600 . ?
C7 C11 1.423(2) . ?
C7 C8 1.438(2) . ?
N5 C14 1.480(2) . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
N5 H5C 0.8900 . ?
C13 C14 1.514(2) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
N4 C12 1.146(2) . ?
C11 N3 1.145(2) . ?
C5 C4 1.370(2) . ?
C5 H5 0.9300 . ?
C4 C3 1.386(2) . ?
C4 H4 0.9300 . ?
C10 C12 1.422(2) . ?
C10 C9 1.430(2) . ?
C3 C2 1.389(2) . ?
C1 C2 1.370(2) . ?
C1 H1A 0.9300 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C2 H2 0.9300 . ?

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
C9 N2 C8 124.91(12) . . ?
C9 N2 C13 117.65(13) . . ?
C8 N2 C13 117.40(13) . . ?
C7 C6 C10 119.65(13) . . ?
C7 C6 C3 119.79(13) . . ?
C10 C6 C3 120.55(13) . . ?
C1 N1 C5 122.50(14) . . ?
C1 N1 H1 118.8 . . ?
C5 N1 H1 118.8 . . ?
C6 C7 C11 123.21(14) . . ?
C6 C7 C8 121.79(13) . . ?
C11 C7 C8 115.00(14) . . ?
C14 N5 H5A 109.5 . . ?
C14 N5 H5B 109.5 . . ?
H5A N5 H5B 109.5 . . ?
C14 N5 H5C 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
N2 C13 C14 109.88(13) . . ?
N2 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
N2 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N3 C11 C7 178.03(16) . . ?
N1 C5 C4 119.91(15) . . ?
N1 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C4 C3 119.43(15) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C10 C12 124.01(14) . . ?
C6 C10 C9 120.86(14) . . ?
C12 C10 C9 115.04(13) . . ?
C4 C3 C2 118.66(14) . . ?
C4 C3 C6 120.53(13) . . ?
C2 C3 C6 120.80(13) . . ?
O2 C9 N2 118.82(13) . . ?
O2 C9 C10 124.16(14) . . ?
N2 C9 C10 117.02(13) . . ?
N4 C12 C10 176.97(17) . . ?
N1 C1 C2 119.96(15) . . ?
N1 C1 H1A 120.0 . . ?
C2 C1 H1A 120.0 . . ?
N5 C14 C13 108.80(13) . . ?
N5 C14 H14A 109.9 . . ?
C13 C14 H14A 109.9 . . ?
N5 C14 H14B 109.9 . . ?
C13 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
C1 C2 C3 119.46(15) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
O1 C8 N2 120.12(14) . . ?
O1 C8 C7 124.16(14) . . ?
N2 C8 C7 115.71(13) . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_hbf4-revised
_database_code_depnum_ccdc_archive 'CCDC 1857444'
_audit_update_record             
;
2018-07-22 deposited with the CCDC.	2019-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 B F4 N5 O4'
_chemical_formula_weight         405.13

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'
B B 0.0013 0.0007 '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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P21/c

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

_cell_length_a                   12.6386(3)
_cell_length_b                   12.6389(4)
_cell_length_c                   11.2764(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.9830(10)
_cell_angle_gamma                90.00
_cell_volume                     1740.03(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1830
_cell_measurement_theta_min      1.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       block
_exptl_crystal_colour            pale-yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832
_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'Bruker SMART APEX II CCD area-detector'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22670
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2998
_reflns_number_gt                2580
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'APEX2(Bruker,2007)and SAINT (Bruker,2007)'
_computing_data_reduction        'SAINT(Bruker,2007)and XPREP(Bruker,2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
;    
ORTEP-3 for Windows (Farrugia, 1997), DIAMOND (Brandenburg,
1999) and Mercury (Macrae et al., 2006)
;
_computing_publication_material  'PLATON (Spek, 2009)'

_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)+(0.0605P)²+0.7933P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2998
_refine_ls_number_parameters     280
_refine_ls_number_restraints     461
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1130
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.005
_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
B1 B 0.0989(2) 0.7117(2) 0.5955(2) 0.0531(6) Uani 1 1 d U . .
F1 F -0.01099(15) 0.72090(19) 0.5461(2) 0.1238(8) Uani 1 1 d U A .
F2 F 0.1310(5) 0.7165(5) 0.4896(4) 0.1029(19) Uani 0.50 1 d PU A 1
F2A F 0.1625(6) 0.7544(6) 0.5392(10) 0.191(4) Uani 0.50 1 d PU A 2
F3 F 0.1417(5) 0.6370(6) 0.6682(7) 0.144(3) Uani 0.50 1 d PU A 1
F3A F 0.1165(5) 0.6018(4) 0.5917(6) 0.1179(19) Uani 0.50 1 d PU A 2
F4 F 0.1379(3) 0.8112(3) 0.6496(4) 0.0930(10) Uani 0.50 1 d PU A 1
F4A F 0.1083(5) 0.7293(6) 0.7135(4) 0.147(2) Uani 0.50 1 d PU A 2
O2 O 0.41759(9) 0.88300(10) 0.60367(11) 0.0365(3) Uani 1 1 d U . .
N2 N 0.47923(10) 0.83134(10) 0.43973(12) 0.0297(3) Uani 1 1 d U . .
O1 O 0.53744(10) 0.78865(10) 0.27062(11) 0.0411(3) Uani 1 1 d U . .
N5 N 0.42340(11) 0.60714(11) 0.36568(13) 0.0359(3) Uani 1 1 d U . .
H5A H 0.4198 0.6188 0.2869 0.054 Uiso 1 1 calc R . .
H5B H 0.4038 0.5407 0.3753 0.054 Uiso 1 1 calc R . .
H5C H 0.4916 0.6178 0.4105 0.054 Uiso 1 1 calc R . .
N1 N 1.00748(12) 1.00745(12) 0.72364(14) 0.0409(4) Uani 1 1 d U . .
H1 H 1.0727 1.0295 0.7576 0.049 Uiso 1 1 calc R . .
C9 C 0.49529(13) 0.87434(12) 0.55755(14) 0.0291(4) Uani 1 1 d U . .
C3 C 0.80199(13) 0.93885(13) 0.61754(14) 0.0295(3) Uani 1 1 d U . .
C7 C 0.66664(13) 0.86231(13) 0.43849(15) 0.0302(4) Uani 1 1 d U . .
C13 C 0.36808(13) 0.79445(13) 0.37662(16) 0.0343(4) Uani 1 1 d U . .
H13A H 0.3575 0.8013 0.2887 0.041 Uiso 1 1 calc R . .
H13B H 0.3146 0.8393 0.4001 0.041 Uiso 1 1 calc R . .
N3 N 0.81254(13) 0.85512(14) 0.31776(15) 0.0486(4) Uani 1 1 d U . .
C6 C 0.68888(13) 0.90148(12) 0.55735(14) 0.0289(3) Uani 1 1 d U . .
C14 C 0.34805(13) 0.68086(14) 0.40646(16) 0.0352(4) Uani 1 1 d U . .
H14A H 0.3583 0.6737 0.4944 0.042 Uiso 1 1 calc R . .
H14B H 0.2729 0.6620 0.3665 0.042 Uiso 1 1 calc R . .
C8 C 0.55979(13) 0.82553(12) 0.37537(15) 0.0302(4) Uani 1 1 d U . .
N4 N 0.63449(15) 0.98961(15) 0.83113(15) 0.0530(5) Uani 1 1 d U . .
C12 C 0.62265(13) 0.95223(14) 0.73593(16) 0.0353(4) Uani 1 1 d U . .
C4 C 0.84555(14) 1.02375(13) 0.56806(15) 0.0339(4) Uani 1 1 d U . .
H4 H 0.8046 1.0574 0.4977 0.041 Uiso 1 1 calc R . .
C10 C 0.60566(13) 0.90740(13) 0.61642(14) 0.0301(4) Uani 1 1 d U . .
C1 C 0.96931(15) 0.92547(16) 0.77257(18) 0.0450(5) Uani 1 1 d U . .
H1A H 1.0130 0.8925 0.8418 0.054 Uiso 1 1 calc R . .
C5 C 0.94928(14) 1.05745(14) 0.62385(17) 0.0389(4) Uani 1 1 d U . .
H5 H 0.9791 1.1149 0.5924 0.047 Uiso 1 1 calc R . .
C2 C 0.86539(15) 0.88906(15) 0.72128(16) 0.0397(4) Uani 1 1 d U . .
H2 H 0.8378 0.8318 0.7556 0.048 Uiso 1 1 calc R . .
C11 C 0.74808(13) 0.85748(14) 0.37270(15) 0.0339(4) Uani 1 1 d U . .
O3 O 0.60655(10) 0.88752(10) 0.07935(12) 0.0434(3) Uani 1 1 d U . .
H3A H 0.6798 0.8838 0.0803 0.065 Uiso 1 1 d R . .
H3B H 0.5981 0.8522 0.1439 0.065 Uiso 1 1 d R . .
O4 O 0.82358(12) 0.57090(17) 0.55647(14) 0.0729(5) Uani 1 1 d U . .
H4A H 0.8070 0.5443 0.4829 0.109 Uiso 1 1 d R . .
H4B H 0.8796 0.6217 0.5411 0.109 Uiso 1 1 d 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
B1 F2A 1.266(6) . ?
B1 F3 1.276(5) . ?
B1 F4A 1.324(5) . ?
B1 F2 1.357(5) . ?
B1 F1 1.362(3) . ?
B1 F3A 1.408(5) . ?
B1 F4 1.429(4) . ?
O2 C9 1.2292(19) . ?
N2 C8 1.397(2) . ?
N2 C9 1.401(2) . ?
N2 C13 1.477(2) . ?
O1 C8 1.233(2) . ?
N5 C14 1.488(2) . ?
N1 C1 1.322(3) . ?
N1 C5 1.334(2) . ?
C9 C10 1.443(2) . ?
C3 C2 1.386(2) . ?
C3 C4 1.387(2) . ?
C3 C6 1.492(2) . ?
C7 C6 1.388(2) . ?
C7 C11 1.417(2) . ?
C7 C8 1.432(2) . ?
C13 C14 1.511(2) . ?
N3 C11 1.144(2) . ?
C6 C10 1.385(2) . ?
N4 C12 1.147(2) . ?
C12 C10 1.426(2) . ?
C4 C5 1.367(2) . ?
C1 C2 1.371(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
F2A B1 F3 114.8(5) . . ?
F2A B1 F4A 121.9(6) . . ?
F3 B1 F4A 64.2(4) . . ?
F2A B1 F2 33.7(5) . . ?
F3 B1 F2 115.2(5) . . ?
F4A B1 F2 155.1(5) . . ?
F2A B1 F1 118.1(4) . . ?
F3 B1 F1 123.0(3) . . ?
F4A B1 F1 102.3(3) . . ?
F2 B1 F1 98.1(3) . . ?
F2A B1 F3A 106.3(5) . . ?
F3 B1 F3A 41.0(4) . . ?
F4A B1 F3A 102.8(4) . . ?
F2 B1 F3A 86.2(4) . . ?
F1 B1 F3A 103.0(3) . . ?
F2A B1 F4 69.2(5) . . ?
F3 B1 F4 109.6(4) . . ?
F4A B1 F4 59.4(3) . . ?
F2 B1 F4 100.8(3) . . ?
F1 B1 F4 107.6(3) . . ?
F3A B1 F4 147.2(4) . . ?
C8 N2 C9 124.54(13) . . ?
C8 N2 C13 117.61(13) . . ?
C9 N2 C13 117.78(13) . . ?
C1 N1 C5 122.83(15) . . ?
O2 C9 N2 120.01(14) . . ?
O2 C9 C10 124.23(15) . . ?
N2 C9 C10 115.75(14) . . ?
C2 C3 C4 119.19(15) . . ?
C2 C3 C6 121.13(15) . . ?
C4 C3 C6 119.68(14) . . ?
C6 C7 C11 121.86(14) . . ?
C6 C7 C8 121.70(15) . . ?
C11 C7 C8 116.44(14) . . ?
N2 C13 C14 112.71(13) . . ?
C10 C6 C7 119.64(15) . . ?
C10 C6 C3 121.45(14) . . ?
C7 C6 C3 118.90(14) . . ?
N5 C14 C13 111.64(14) . . ?
O1 C8 N2 120.04(14) . . ?
O1 C8 C7 123.52(15) . . ?
N2 C8 C7 116.44(14) . . ?
N4 C12 C10 178.6(2) . . ?
C5 C4 C3 119.26(16) . . ?
C6 C10 C12 121.91(15) . . ?
C6 C10 C9 121.81(15) . . ?
C12 C10 C9 116.18(14) . . ?
N1 C1 C2 120.01(17) . . ?
N1 C5 C4 119.65(16) . . ?
C1 C2 C3 119.04(17) . . ?
N3 C11 C7 178.5(2) . . ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.401
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.040
