# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

####################################################################### 
# 
# 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
_database_code_depnum_ccdc_archive 'CCDC 1524278'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H4 F2 N4 O12'
_chemical_formula_sum            'C6 H4 F2 N4 O12'
_chemical_formula_weight         362.13

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   6.1749(7)
_cell_length_b                   6.3972(7)
_cell_length_c                   9.0143(10)
_cell_angle_alpha                78.006(4)
_cell_angle_beta                 80.204(4)
_cell_angle_gamma                63.912(4)
_cell_volume                     311.56(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    171(2)
_cell_measurement_reflns_used    1077
_cell_measurement_theta_min      3.59
_cell_measurement_theta_max      25.22

_exptl_crystal_description       column
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.930
_exptl_crystal_F_000             182
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.206
_shelx_estimated_absorpt_T_min   0.929
_shelx_estimated_absorpt_T_max   0.968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6562
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      171(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2739
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.587
_diffrn_reflns_theta_max         25.375
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             1131
_reflns_number_gt                879
_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-2014/7 (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)+(0.0356P)²+0.0537P] 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         1131
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0568
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.0784
_refine_ls_wR_factor_gt          0.0729
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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
C1 C 0.3849(4) 0.5177(3) 0.9681(2) 0.0170(4) Uani 1 1 d . . . . .
C2 C 0.2501(4) 0.4501(3) 0.7600(2) 0.0196(4) Uani 1 1 d . . . . .
H2A H 0.2540 0.5243 0.6523 0.024 Uiso 1 1 calc R U . . .
H2B H 0.0918 0.5415 0.8131 0.024 Uiso 1 1 calc R U . . .
C3 C 0.2909(3) 0.1970(3) 0.7712(2) 0.0184(4) Uani 1 1 d . . . . .
F1 F 0.3071(2) 0.08301(19) 0.91259(12) 0.0267(3) Uani 1 1 d . . . . .
N1 N 0.0911(3) 0.1744(3) 0.70569(18) 0.0214(4) Uani 1 1 d . . . . .
N2 N 0.5254(3) 0.0564(3) 0.6778(2) 0.0260(4) Uani 1 1 d . . . . .
O1 O 0.4460(2) 0.4402(2) 0.83274(15) 0.0215(3) Uani 1 1 d . . . . .
O2 O -0.0282(3) 0.3407(3) 0.61805(17) 0.0366(4) Uani 1 1 d . . . . .
O3 O 0.0701(3) -0.0087(3) 0.74740(18) 0.0364(4) Uani 1 1 d . . . . .
O4 O 0.5637(3) 0.1595(3) 0.55352(17) 0.0366(4) Uani 1 1 d . . . . .
O5 O 0.6477(3) -0.1427(3) 0.7335(2) 0.0431(5) Uani 1 1 d . . . . .
O6 O 0.1868(2) 0.6004(2) 1.03003(15) 0.0255(4) 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
C1 O6 1.187(2) . ?
C1 O1 1.345(2) . ?
C1 C1 1.531(4) 2_667 ?
C2 O1 1.443(2) . ?
C2 C3 1.509(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 F1 1.326(2) . ?
C3 N1 1.528(2) . ?
C3 N2 1.539(3) . ?
N1 O2 1.207(2) . ?
N1 O3 1.2097(19) . ?
N2 O5 1.209(2) . ?
N2 O4 1.219(2) . ?

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
O6 C1 O1 126.66(17) . . ?
O6 C1 C1 124.7(2) . 2_667 ?
O1 C1 C1 108.7(2) . 2_667 ?
O1 C2 C3 105.10(15) . . ?
O1 C2 H2A 110.7 . . ?
C3 C2 H2A 110.7 . . ?
O1 C2 H2B 110.7 . . ?
C3 C2 H2B 110.7 . . ?
H2A C2 H2B 108.8 . . ?
F1 C3 C2 113.39(15) . . ?
F1 C3 N1 107.45(14) . . ?
C2 C3 N1 112.31(15) . . ?
F1 C3 N2 106.74(15) . . ?
C2 C3 N2 111.71(15) . . ?
N1 C3 N2 104.70(14) . . ?
O2 N1 O3 127.21(17) . . ?
O2 N1 C3 116.54(15) . . ?
O3 N1 C3 116.25(15) . . ?
O5 N2 O4 127.45(19) . . ?
O5 N2 C3 117.19(17) . . ?
O4 N2 C3 115.34(16) . . ?
C1 O1 C2 115.85(15) . . ?

_refine_diff_density_max         0.192
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1560633'
_audit_update_record             
;
2017-07-06 deposited with the CCDC.
2017-09-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H4 F N5 O12'
_chemical_formula_sum            'C9 H4 F N5 O12'
_chemical_formula_weight         393.17

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.8921(6)
_cell_length_b                   12.6006(16)
_cell_length_c                   18.796(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1395.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1439
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      23.87

_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.871
_exptl_crystal_F_000             792
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.185
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6186
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'PHOTON 100 CMOS detector'
_diffrn_measurement_method       'omega scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10581
_diffrn_reflns_av_unetI/netI     0.1064
_diffrn_reflns_av_R_equivalents  0.1265
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.233
_diffrn_reflns_theta_max         25.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2556
_reflns_number_gt                1622
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_max     0.998
_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-2014/7 (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)+(0.0277P)²] 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_abs_structure_details 
;
 Flack x determined using 481 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2556
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1163
_refine_ls_R_factor_gt           0.0514
_refine_ls_wR_factor_ref         0.0914
_refine_ls_wR_factor_gt          0.0740
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
C1 C 0.4850(10) 0.7813(4) 0.6948(3) 0.0182(14) Uani 1 1 d . . . . .
C2 C 0.3101(9) 0.7080(5) 0.7068(3) 0.0190(14) Uani 1 1 d . . . . .
C3 C 0.3061(10) 0.6219(5) 0.6600(3) 0.0203(14) Uani 1 1 d . . . . .
C4 C 0.4623(9) 0.6056(5) 0.6072(3) 0.0194(14) Uani 1 1 d . . . . .
H4 H 0.4552 0.5451 0.5772 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6309(10) 0.6812(4) 0.5996(3) 0.0193(14) Uani 1 1 d . . . . .
C6 C 0.6452(10) 0.7703(4) 0.6417(3) 0.0182(14) Uani 1 1 d . . . . .
H6 H 0.7602 0.8221 0.6345 0.022 Uiso 1 1 calc R U . . .
C7 C 0.1357(10) 0.7279(5) 0.7640(3) 0.0221(15) Uani 1 1 d . . . . .
C8 C 0.0661(10) 0.6988(5) 0.8856(3) 0.0255(15) Uani 1 1 d . . . . .
H8A H 0.0016 0.7710 0.8814 0.031 Uiso 1 1 calc R U . . .
H8B H 0.1671 0.6970 0.9276 0.031 Uiso 1 1 calc R U . . .
C9 C -0.1221(9) 0.6189(5) 0.8943(3) 0.0236(14) Uani 1 1 d . . . . .
F1 F -0.2803(6) 0.6234(3) 0.8447(2) 0.0327(9) Uani 1 1 d . . . . .
N1 N 0.5082(8) 0.8746(4) 0.7415(3) 0.0215(12) Uani 1 1 d . . . . .
N2 N -0.2390(9) 0.6332(4) 0.9664(3) 0.0287(13) Uani 1 1 d . . . . .
N3 N -0.0268(9) 0.5050(4) 0.8941(3) 0.0248(12) Uani 1 1 d . . . . .
N4 N 0.1180(9) 0.5438(4) 0.6647(3) 0.0251(13) Uani 1 1 d . . . . .
N5 N 0.8085(9) 0.6650(4) 0.5457(3) 0.0268(14) Uani 1 1 d . . . . .
O1 O 0.6158(7) 0.9509(3) 0.7186(2) 0.0289(11) Uani 1 1 d . . . . .
O2 O 0.4243(7) 0.8702(4) 0.8009(2) 0.0339(11) Uani 1 1 d . . . . .
O3 O 0.1924(7) 0.6732(3) 0.8228(2) 0.0214(10) Uani 1 1 d . . . . .
O4 O -0.0220(7) 0.7860(3) 0.7573(2) 0.0280(11) Uani 1 1 d . . . . .
O5 O -0.1128(8) 0.6403(4) 1.0183(2) 0.0383(13) Uani 1 1 d . . . . .
O6 O -0.4438(8) 0.6369(4) 0.9671(3) 0.0459(14) Uani 1 1 d . . . . .
O7 O 0.1382(8) 0.4914(3) 0.9324(2) 0.0331(12) Uani 1 1 d . . . . .
O8 O -0.1212(8) 0.4409(3) 0.8575(2) 0.0380(13) Uani 1 1 d . . . . .
O9 O -0.0334(7) 0.5614(3) 0.7085(3) 0.0330(12) Uani 1 1 d . . . . .
O10 O 0.1226(8) 0.4681(4) 0.6241(3) 0.0415(14) Uani 1 1 d . . . . .
O11 O 0.7902(8) 0.5914(4) 0.5041(3) 0.0385(13) Uani 1 1 d . . . . .
O12 O 0.9705(7) 0.7265(4) 0.5457(2) 0.0346(12) 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
C1 C6 1.381(8) . ?
C1 C2 1.402(7) . ?
C1 N1 1.474(7) . ?
C2 C3 1.397(8) . ?
C2 C7 1.509(8) . ?
C3 C4 1.368(8) . ?
C3 N4 1.485(7) . ?
C4 C5 1.383(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.377(8) . ?
C5 N5 1.470(8) . ?
C6 H6 0.9500 . ?
C7 O4 1.190(7) . ?
C7 O3 1.344(6) . ?
C8 O3 1.432(7) . ?
C8 C9 1.506(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 F1 1.319(7) . ?
C9 N2 1.531(8) . ?
C9 N3 1.541(7) . ?
N1 O2 1.221(6) . ?
N1 O1 1.230(6) . ?
N2 O6 1.207(6) . ?
N2 O5 1.230(7) . ?
N3 O8 1.199(6) . ?
N3 O7 1.221(6) . ?
N4 O10 1.221(6) . ?
N4 O9 1.234(6) . ?
N5 O11 1.217(6) . ?
N5 O12 1.229(6) . ?

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 C1 C2 123.5(5) . . ?
C6 C1 N1 116.6(5) . . ?
C2 C1 N1 119.9(5) . . ?
C3 C2 C1 115.0(6) . . ?
C3 C2 C7 124.5(5) . . ?
C1 C2 C7 120.4(5) . . ?
C4 C3 C2 124.1(6) . . ?
C4 C3 N4 116.5(5) . . ?
C2 C3 N4 119.3(6) . . ?
C3 C4 C5 117.1(5) . . ?
C3 C4 H4 121.4 . . ?
C5 C4 H4 121.4 . . ?
C6 C5 C4 123.0(6) . . ?
C6 C5 N5 117.8(5) . . ?
C4 C5 N5 119.2(5) . . ?
C5 C6 C1 117.1(5) . . ?
C5 C6 H6 121.4 . . ?
C1 C6 H6 121.4 . . ?
O4 C7 O3 126.6(6) . . ?
O4 C7 C2 124.0(6) . . ?
O3 C7 C2 109.4(5) . . ?
O3 C8 C9 108.8(5) . . ?
O3 C8 H8A 109.9 . . ?
C9 C8 H8A 109.9 . . ?
O3 C8 H8B 109.9 . . ?
C9 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
F1 C9 C8 114.5(5) . . ?
F1 C9 N2 107.6(5) . . ?
C8 C9 N2 110.5(5) . . ?
F1 C9 N3 107.2(5) . . ?
C8 C9 N3 110.7(5) . . ?
N2 C9 N3 105.9(5) . . ?
O2 N1 O1 124.4(5) . . ?
O2 N1 C1 118.0(5) . . ?
O1 N1 C1 117.6(5) . . ?
O6 N2 O5 126.4(6) . . ?
O6 N2 C9 117.6(6) . . ?
O5 N2 C9 116.0(5) . . ?
O8 N3 O7 127.8(5) . . ?
O8 N3 C9 117.4(5) . . ?
O7 N3 C9 114.8(5) . . ?
O10 N4 O9 125.0(5) . . ?
O10 N4 C3 117.6(5) . . ?
O9 N4 C3 117.4(5) . . ?
O11 N5 O12 123.3(6) . . ?
O11 N5 C5 119.0(5) . . ?
O12 N5 C5 117.7(5) . . ?
C7 O3 C8 115.7(5) . . ?

_refine_diff_density_max         0.237
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.065

