# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_201707-31a
_database_code_depnum_ccdc_archive 'CCDC 1589971'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.	2022-12-20 downloaded from the CCDC.
;
_audit_creation_date             2017-07-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5370)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Cl2 F4 N10'
_chemical_formula_sum            'C10 H8 Cl2 F4 N10'
_chemical_formula_weight         415.16
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.950(2)
_cell_length_b                   7.2595(15)
_cell_length_c                   9.6370(19)
_cell_angle_alpha                90
_cell_angle_beta                 97.03(3)
_cell_angle_gamma                90
_cell_volume                     760.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2497
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      27.4739
_cell_measurement_theta_min      2.1293
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.895
_exptl_absorpt_coefficient_mu    0.494
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8187
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5728
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         3.375
_diffrn_ambient_temperature      153.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1662
_reflns_number_total             1726
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.539
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.133
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         1726
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.137
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0331P)²+0.9628P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1062
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 C5-C4 = C5-C4A = C5-C3A = C5-C3
 1.54 with sigma of 0.02
 N5-C4A = N5-C4 = N5-C3 = N5-C3A
 1.47 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
F2A \\sim F2 \\sim C3 \\sim C3A \\sim C4A \\sim C4: within 1.7A with sigma of
0.01 and sigma for terminal atoms of 0.01
Uanis(C3) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C4A) \\sim Ueq, Uanis(C4)
\\sim Ueq, Uanis(F2A) \\sim Ueq, Uanis(F2) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.01
4. Others
 Sof(F2A)=1-FVAR(1)
 Sof(F2)=FVAR(1)
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=1-FVAR(2)
 Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C4A(H4AA,H4AB), C3A(H3AA,H3AB)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.22640(4) 0.25756(7) 0.59745(7) 0.02738(18) Uani 1 1 d . . . . .
F1 F -0.51107(12) 0.2135(2) 0.55556(18) 0.0417(4) Uani 1 1 d . . . . .
F2 F -0.4416(8) 0.136(2) 0.7682(9) 0.055(2) Uani 0.53(3) 1 d . U P A 1
N1 N -0.04827(15) 0.0418(2) 0.50935(18) 0.0187(4) Uani 1 1 d . . . . .
N2 N -0.02498(15) 0.2109(2) 0.57150(18) 0.0177(4) Uani 1 1 d . . . . .
N3 N -0.07768(16) 0.4693(3) 0.6719(2) 0.0233(4) Uani 1 1 d . . . . .
N4 N 0.05156(16) 0.4654(3) 0.6743(2) 0.0228(4) Uani 1 1 d . . . . .
N5 N -0.24186(16) 0.2784(3) 0.5774(2) 0.0229(4) Uani 1 1 d D . . . .
C1 C 0.07999(18) 0.3143(3) 0.6176(2) 0.0195(4) Uani 1 1 d . . . . .
C2 C -0.11978(18) 0.3178(3) 0.6105(2) 0.0194(4) Uani 1 1 d . . . . .
C3 C -0.2996(11) 0.1068(18) 0.6272(16) 0.031(2) Uani 0.48(2) 1 d D U P A 1
H3A H -0.3155 0.0104 0.5546 0.038 Uiso 0.48(2) 1 calc R . P A 1
H3B H -0.2558 0.0555 0.7146 0.038 Uiso 0.48(2) 1 calc R . P A 1
C4 C -0.3391(9) 0.3979(14) 0.6218(14) 0.0234(18) Uani 0.48(2) 1 d D U P A 1
H4A H -0.3812 0.4761 0.5465 0.028 Uiso 0.48(2) 1 calc R . P A 1
H4B H -0.3132 0.4706 0.7073 0.028 Uiso 0.48(2) 1 calc R . P A 1
C5 C -0.4085(2) 0.2165(4) 0.6480(3) 0.0306(5) Uani 1 1 d D . . . .
F2A F -0.4549(10) 0.217(3) 0.7714(10) 0.060(2) Uani 0.47(3) 1 d . U P A 2
C4A C -0.3248(9) 0.3789(16) 0.6670(15) 0.030(2) Uani 0.52(2) 1 d D U P A 2
H4AA H -0.2877 0.3992 0.7647 0.037 Uiso 0.52(2) 1 calc R . P A 2
H4AB H -0.3609 0.4940 0.6247 0.037 Uiso 0.52(2) 1 calc R . P A 2
C3A C -0.3062(10) 0.1028(15) 0.5869(13) 0.0221(18) Uani 0.52(2) 1 d D U P A 2
H3AA H -0.2627 0.0139 0.6534 0.027 Uiso 0.52(2) 1 calc R . P A 2
H3AB H -0.3333 0.0445 0.4955 0.027 Uiso 0.52(2) 1 calc R . P 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 C1 1.689(2) . ?
F1 C5 1.345(3) . ?
F2 C5 1.385(9) . ?
N1 N1 1.251(3) 3_556 ?
N1 N2 1.376(2) . ?
N2 C1 1.399(3) . ?
N2 C2 1.384(3) . ?
N3 N4 1.413(2) . ?
N3 C2 1.306(3) . ?
N4 C1 1.281(3) . ?
N5 C2 1.366(3) . ?
N5 C3 1.502(13) . ?
N5 C4 1.477(10) . ?
N5 C4A 1.515(9) . ?
N5 C3A 1.465(11) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C3 C5 1.468(13) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4 C5 1.557(10) . ?
C5 F2A 1.348(9) . ?
C5 C4A 1.491(10) . ?
C5 C3A 1.564(10) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?

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
N1 N1 N2 112.4(2) 3_556 . ?
N1 N2 C1 135.90(17) . . ?
N1 N2 C2 120.87(16) . . ?
C2 N2 C1 103.14(17) . . ?
C2 N3 N4 106.73(17) . . ?
C1 N4 N3 107.79(17) . . ?
C2 N5 C3 122.5(5) . . ?
C2 N5 C4 121.9(4) . . ?
C2 N5 C4A 113.9(4) . . ?
C2 N5 C3A 129.2(4) . . ?
C4 N5 C3 92.7(6) . . ?
C3A N5 C4A 93.3(6) . . ?
N2 C1 Cl1 125.96(16) . . ?
N4 C1 Cl1 122.79(16) . . ?
N4 C1 N2 111.20(18) . . ?
N3 C2 N2 111.11(18) . . ?
N3 C2 N5 124.27(19) . . ?
N5 C2 N2 124.35(19) . . ?
N5 C3 H3A 113.9 . . ?
N5 C3 H3B 113.9 . . ?
H3A C3 H3B 111.1 . . ?
C5 C3 N5 88.6(7) . . ?
C5 C3 H3A 113.9 . . ?
C5 C3 H3B 113.9 . . ?
N5 C4 H4A 114.3 . . ?
N5 C4 H4B 114.3 . . ?
N5 C4 C5 86.2(5) . . ?
H4A C4 H4B 111.4 . . ?
C5 C4 H4A 114.3 . . ?
C5 C4 H4B 114.3 . . ?
F1 C5 F2 105.3(4) . . ?
F1 C5 C3 121.8(6) . . ?
F1 C5 C4 106.9(5) . . ?
F1 C5 F2A 102.1(5) . . ?
F1 C5 C4A 123.0(6) . . ?
F1 C5 C3A 108.7(5) . . ?
F2 C5 C3 100.7(8) . . ?
F2 C5 C4 132.6(8) . . ?
C3 C5 C4 90.9(6) . . ?
F2A C5 C4A 100.6(8) . . ?
F2A C5 C3A 134.2(10) . . ?
C4A C5 C3A 90.3(6) . . ?
N5 C4A H4AA 114.1 . . ?
N5 C4A H4AB 114.1 . . ?
C5 C4A N5 87.2(5) . . ?
C5 C4A H4AA 114.1 . . ?
C5 C4A H4AB 114.1 . . ?
H4AA C4A H4AB 111.3 . . ?
N5 C3A C5 86.4(6) . . ?
N5 C3A H3AA 114.3 . . ?
N5 C3A H3AB 114.3 . . ?
C5 C3A H3AA 114.3 . . ?
C5 C3A H3AB 114.3 . . ?
H3AA C3A H3AB 111.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F1 C5 C4A N5 -100.4(6) . . . . ?
F1 C5 C3A N5 112.5(4) . . . . ?
N1 N1 N2 C1 1.0(4) 3_556 . . . ?
N1 N1 N2 C2 -175.0(2) 3_556 . . . ?
N1 N2 C1 Cl1 4.8(4) . . . . ?
N1 N2 C1 N4 -177.7(2) . . . . ?
N1 N2 C2 N3 177.71(18) . . . . ?
N1 N2 C2 N5 -8.0(3) . . . . ?
N3 N4 C1 Cl1 178.97(15) . . . . ?
N3 N4 C1 N2 1.4(2) . . . . ?
N4 N3 C2 N2 0.2(2) . . . . ?
N4 N3 C2 N5 -174.1(2) . . . . ?
N5 C3 C5 F1 101.2(6) . . . . ?
N5 C3 C5 F2 -143.1(8) . . . . ?
N5 C3 C5 C4 -9.4(5) . . . . ?
N5 C4 C5 F1 -114.2(4) . . . . ?
N5 C4 C5 F2 115.0(9) . . . . ?
N5 C4 C5 C3 9.6(5) . . . . ?
C1 N2 C2 N3 0.6(2) . . . . ?
C1 N2 C2 N5 174.8(2) . . . . ?
C2 N2 C1 Cl1 -178.72(16) . . . . ?
C2 N2 C1 N4 -1.2(2) . . . . ?
C2 N3 N4 C1 -1.0(2) . . . . ?
C2 N5 C3 C5 141.1(4) . . . . ?
C2 N5 C4 C5 -141.0(3) . . . . ?
C2 N5 C4A C5 -149.0(4) . . . . ?
C2 N5 C3A C5 137.2(3) . . . . ?
C3 N5 C2 N2 62.4(8) . . . . ?
C3 N5 C2 N3 -124.0(7) . . . . ?
C3 N5 C4 C5 -9.4(5) . . . . ?
C4 N5 C2 N2 -179.9(6) . . . . ?
C4 N5 C2 N3 -6.4(7) . . . . ?
C4 N5 C3 C5 9.9(5) . . . . ?
F2A C5 C4A N5 147.5(9) . . . . ?
F2A C5 C3A N5 -117.9(9) . . . . ?
C4A N5 C2 N2 162.1(6) . . . . ?
C4A N5 C2 N3 -24.4(7) . . . . ?
C4A N5 C3A C5 12.5(5) . . . . ?
C4A C5 C3A N5 -12.7(5) . . . . ?
C3A N5 C2 N2 45.9(7) . . . . ?
C3A N5 C2 N3 -140.6(6) . . . . ?
C3A N5 C4A C5 -13.1(5) . . . . ?
C3A C5 C4A N5 12.3(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1589972'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.	2022-12-20 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         ?
_chemical_formula_sum            'C9 H10 Cl2 F2 N8'
_chemical_formula_weight         339.15

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'
F F 0.0171 0.0103 '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'

_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                   7.6743(13)
_cell_length_b                   8.1690(14)
_cell_length_c                   11.2815(19)
_cell_angle_alpha                92.753(4)
_cell_angle_beta                 93.733(4)
_cell_angle_gamma                93.499(4)
_cell_volume                     703.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1207
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      22.55

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             344
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.491
_shelx_estimated_absorpt_T_min   0.900
_shelx_estimated_absorpt_T_max   0.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4343
_diffrn_reflns_av_unetI/netI     0.0399
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.501
_diffrn_reflns_theta_max         25.058
_diffrn_reflns_theta_full        25.058
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             2461
_reflns_number_gt                1871
_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)+(0.0838P)²+0.0327P] 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         2461
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0571
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1343
_refine_ls_wR_factor_gt          0.1196
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.972
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.001

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 0.3726(3) 0.4355(3) 0.6431(2) 0.0413(6) Uani 1 1 d . . . . .
C2 C 0.5877(3) 0.2868(3) 0.5942(2) 0.0415(6) Uani 1 1 d . . . . .
C3 C 0.7603(5) 0.0884(4) 0.5051(3) 0.0764(11) Uani 1 1 d . . . . .
H3A H 0.6491 0.0356 0.4768 0.115 Uiso 1 1 calc R U . . .
H3B H 0.8372 0.0072 0.5316 0.115 Uiso 1 1 calc R U . . .
H3C H 0.8104 0.1456 0.4418 0.115 Uiso 1 1 calc R U . . .
C4 C 0.8971(4) 0.2934(4) 0.6529(3) 0.0710(10) Uani 1 1 d . . . . .
H4A H 0.9604 0.3359 0.5893 0.106 Uiso 1 1 calc R U . . .
H4B H 0.9674 0.2198 0.6959 0.106 Uiso 1 1 calc R U . . .
H4C H 0.8698 0.3825 0.7057 0.106 Uiso 1 1 calc R U . . .
C5 C 0.5257(3) 0.2645(3) 0.8784(2) 0.0453(6) Uani 1 1 d . . . . .
C6 C 0.6949(3) 0.4868(3) 0.8768(2) 0.0401(6) Uani 1 1 d . . . . .
C7 C 0.9048(4) 0.7256(3) 0.9207(2) 0.0523(7) Uani 1 1 d . . . . .
H7A H 1.0261 0.6981 0.9273 0.063 Uiso 1 1 calc R U . . .
H7B H 0.8594 0.7411 0.9984 0.063 Uiso 1 1 calc R U . . .
C8 C 0.8695(4) 0.8613(4) 0.8391(3) 0.0542(7) Uani 1 1 d . . . . .
C9 C 0.7177(4) 0.7568(4) 0.7763(3) 0.0626(8) Uani 1 1 d . . . . .
H9A H 0.6037 0.7838 0.8010 0.075 Uiso 1 1 calc R U . . .
H9B H 0.7195 0.7494 0.6904 0.075 Uiso 1 1 calc R U . . .
Cl1 Cl 0.25761(9) 0.56401(10) 0.72375(7) 0.0616(3) Uani 1 1 d . . . . .
Cl2 Cl 0.37906(11) 0.10964(10) 0.82747(7) 0.0673(3) Uani 1 1 d . . . . .
F1 F 0.8305(3) 1.0051(2) 0.8907(2) 0.0890(7) Uani 1 1 d . . . . .
F2 F 1.0008(3) 0.8980(3) 0.76915(19) 0.0853(6) Uani 1 1 d . . . . .
N1 N 0.3317(3) 0.3744(3) 0.5378(2) 0.0509(6) Uani 1 1 d . . . . .
N2 N 0.4714(3) 0.2787(3) 0.50584(19) 0.0504(6) Uani 1 1 d . . . . .
N3 N 0.5353(3) 0.3909(3) 0.68545(17) 0.0393(5) Uani 1 1 d . . . . .
N4 N 0.5822(3) 0.3824(3) 0.80458(17) 0.0422(5) Uani 1 1 d . . . . .
N5 N 0.5954(3) 0.2889(3) 0.9841(2) 0.0541(6) Uani 1 1 d . . . . .
N6 N 0.7059(3) 0.4342(3) 0.98393(19) 0.0524(6) Uani 1 1 d . . . . .
N7 N 0.7360(3) 0.2056(3) 0.6043(2) 0.0523(6) Uani 1 1 d . . . . .
N8 N 0.7913(3) 0.6154(3) 0.83634(18) 0.0450(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.279(3) . ?
C1 N3 1.383(3) . ?
C1 Cl1 1.683(3) . ?
C2 N2 1.290(4) . ?
C2 N7 1.353(4) . ?
C2 N3 1.399(3) . ?
C3 N7 1.466(4) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 N7 1.452(4) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 N5 1.276(3) . ?
C5 N4 1.372(3) . ?
C5 Cl2 1.694(3) . ?
C6 N6 1.302(3) . ?
C6 N8 1.362(3) . ?
C6 N4 1.375(3) . ?
C7 N8 1.479(3) . ?
C7 C8 1.500(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 F1 1.344(3) . ?
C8 F2 1.348(3) . ?
C8 C9 1.517(4) . ?
C9 N8 1.489(4) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N1 N2 1.419(3) . ?
N3 N4 1.375(3) . ?
N5 N6 1.416(4) . ?

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
N1 C1 N3 111.5(2) . . ?
N1 C1 Cl1 127.2(2) . . ?
N3 C1 Cl1 121.13(18) . . ?
N2 C2 N7 127.7(2) . . ?
N2 C2 N3 109.4(2) . . ?
N7 C2 N3 122.8(2) . . ?
N7 C3 H3A 109.5 . . ?
N7 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N7 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N7 C4 H4A 109.5 . . ?
N7 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N7 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N5 C5 N4 112.1(2) . . ?
N5 C5 Cl2 127.0(2) . . ?
N4 C5 Cl2 121.0(2) . . ?
N6 C6 N8 126.4(2) . . ?
N6 C6 N4 109.7(2) . . ?
N8 C6 N4 123.6(2) . . ?
N8 C7 C8 87.4(2) . . ?
N8 C7 H7A 114.1 . . ?
C8 C7 H7A 114.1 . . ?
N8 C7 H7B 114.1 . . ?
C8 C7 H7B 114.1 . . ?
H7A C7 H7B 111.3 . . ?
F1 C8 F2 105.8(2) . . ?
F1 C8 C7 116.5(2) . . ?
F2 C8 C7 114.0(3) . . ?
F1 C8 C9 116.3(3) . . ?
F2 C8 C9 114.0(2) . . ?
C7 C8 C9 90.1(2) . . ?
N8 C9 C8 86.5(2) . . ?
N8 C9 H9A 114.2 . . ?
C8 C9 H9A 114.2 . . ?
N8 C9 H9B 114.2 . . ?
C8 C9 H9B 114.2 . . ?
H9A C9 H9B 111.4 . . ?
C1 N1 N2 106.7(2) . . ?
C2 N2 N1 108.3(2) . . ?
N4 N3 C1 123.0(2) . . ?
N4 N3 C2 125.6(2) . . ?
C1 N3 C2 104.0(2) . . ?
C5 N4 N3 126.9(2) . . ?
C5 N4 C6 104.3(2) . . ?
N3 N4 C6 128.8(2) . . ?
C5 N5 N6 106.2(2) . . ?
C6 N6 N5 107.7(2) . . ?
C2 N7 C4 119.1(2) . . ?
C2 N7 C3 115.2(3) . . ?
C4 N7 C3 113.8(2) . . ?
C6 N8 C7 120.2(2) . . ?
C6 N8 C9 125.0(2) . . ?
C7 N8 C9 92.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N8 C7 C8 F1 134.7(3) . . . . ?
N8 C7 C8 F2 -101.5(2) . . . . ?
N8 C7 C8 C9 15.0(2) . . . . ?
F1 C8 C9 N8 -134.8(3) . . . . ?
F2 C8 C9 N8 101.6(3) . . . . ?
C7 C8 C9 N8 -14.9(2) . . . . ?
N3 C1 N1 N2 1.5(3) . . . . ?
Cl1 C1 N1 N2 177.89(19) . . . . ?
N7 C2 N2 N1 175.3(2) . . . . ?
N3 C2 N2 N1 -2.2(3) . . . . ?
C1 N1 N2 C2 0.5(3) . . . . ?
N1 C1 N3 N4 -153.8(2) . . . . ?
Cl1 C1 N3 N4 29.5(3) . . . . ?
N1 C1 N3 C2 -2.7(3) . . . . ?
Cl1 C1 N3 C2 -179.36(18) . . . . ?
N2 C2 N3 N4 153.0(2) . . . . ?
N7 C2 N3 N4 -24.6(4) . . . . ?
N2 C2 N3 C1 2.9(3) . . . . ?
N7 C2 N3 C1 -174.7(2) . . . . ?
N5 C5 N4 N3 178.8(2) . . . . ?
Cl2 C5 N4 N3 -1.5(4) . . . . ?
N5 C5 N4 C6 -0.9(3) . . . . ?
Cl2 C5 N4 C6 178.76(18) . . . . ?
C1 N3 N4 C5 73.2(3) . . . . ?
C2 N3 N4 C5 -71.6(3) . . . . ?
C1 N3 N4 C6 -107.1(3) . . . . ?
C2 N3 N4 C6 108.1(3) . . . . ?
N6 C6 N4 C5 0.7(3) . . . . ?
N8 C6 N4 C5 174.8(2) . . . . ?
N6 C6 N4 N3 -179.0(2) . . . . ?
N8 C6 N4 N3 -5.0(4) . . . . ?
N4 C5 N5 N6 0.7(3) . . . . ?
Cl2 C5 N5 N6 -178.9(2) . . . . ?
N8 C6 N6 N5 -174.2(2) . . . . ?
N4 C6 N6 N5 -0.3(3) . . . . ?
C5 N5 N6 C6 -0.3(3) . . . . ?
N2 C2 N7 C4 137.0(3) . . . . ?
N3 C2 N7 C4 -45.8(4) . . . . ?
N2 C2 N7 C3 -3.6(4) . . . . ?
N3 C2 N7 C3 173.6(2) . . . . ?
N6 C6 N8 C7 -9.2(4) . . . . ?
N4 C6 N8 C7 177.8(2) . . . . ?
N6 C6 N8 C9 -126.3(3) . . . . ?
N4 C6 N8 C9 60.7(4) . . . . ?
C8 C7 N8 C6 -148.4(2) . . . . ?
C8 C7 N8 C9 -15.3(2) . . . . ?
C8 C9 N8 C6 144.8(2) . . . . ?
C8 C9 N8 C7 15.1(2) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.229
_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_20171003_1_0m_5
_database_code_depnum_ccdc_archive 'CCDC 1589973'
_audit_update_record             
;
2017-12-08 deposited with the CCDC.	2022-12-20 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         ?
_chemical_formula_sum            'C10 H8 Cl2 F4 N8'
_chemical_formula_weight         387.14

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'
F F 0.0171 0.0103 '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'

_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                   7.83310(10)
_cell_length_b                   8.63080(10)
_cell_length_c                   11.29240(10)
_cell_angle_alpha                100.6540(10)
_cell_angle_beta                 94.0110(10)
_cell_angle_gamma                94.8510(10)
_cell_volume                     744.724(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    750
_cell_measurement_theta_min      2.41
_cell_measurement_theta_max      21.04

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.726
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.494
_shelx_estimated_absorpt_T_min   0.899
_shelx_estimated_absorpt_T_max   0.916
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            2567
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.842
_diffrn_reflns_theta_max         24.906
_diffrn_reflns_theta_full        24.906
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             2567
_reflns_number_gt                2023
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1272P)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_number_reflns         2567
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0671
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1784
_refine_ls_wR_factor_gt          0.1611
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_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 0.4168(5) 0.3866(5) 0.6331(4) 0.0352(9) Uani 1 1 d . . . . .
C2 C 0.2711(5) 0.5855(5) 0.6077(4) 0.0353(10) Uani 1 1 d . . . . .
C3 C 0.0985(6) 0.7778(5) 0.5377(5) 0.0475(12) Uani 1 1 d . . . . .
H3A H -0.0232 0.7796 0.5483 0.057 Uiso 1 1 calc R U . . .
H3B H 0.1167 0.7227 0.4573 0.057 Uiso 1 1 calc R U . . .
C4 C 0.2007(6) 0.9376(5) 0.5749(4) 0.0445(11) Uani 1 1 d . . . . .
C5 C 0.3122(7) 0.8751(5) 0.6670(5) 0.0565(14) Uani 1 1 d . . . . .
H5A H 0.4295 0.8653 0.6464 0.068 Uiso 1 1 calc R U . . .
H5B H 0.3095 0.9313 0.7495 0.068 Uiso 1 1 calc R U . . .
C6 C 0.2576(6) 0.5255(6) 0.8897(4) 0.0438(11) Uani 1 1 d . . . . .
C7 C 0.4845(6) 0.6910(5) 0.8919(4) 0.0351(10) Uani 1 1 d . . . . .
C8 C 0.7588(6) 0.7090(7) 0.7924(5) 0.0593(14) Uani 1 1 d . . . . .
H8A H 0.7510 0.7007 0.7053 0.071 Uiso 1 1 calc R U . . .
H8B H 0.7856 0.6102 0.8152 0.071 Uiso 1 1 calc R U . . .
C9 C 0.8704(7) 0.8544(7) 0.8624(5) 0.0582(14) Uani 1 1 d . . . . .
C10 C 0.7265(6) 0.8967(6) 0.9420(5) 0.0505(12) Uani 1 1 d . . . . .
H10A H 0.7412 0.8686 1.0211 0.061 Uiso 1 1 calc R U . . .
H10B H 0.6989 1.0052 0.9481 0.061 Uiso 1 1 calc R U . . .
Cl1 Cl 0.54016(18) 0.27516(14) 0.70339(11) 0.0545(4) Uani 1 1 d . . . . .
Cl2 Cl 0.09784(19) 0.37990(18) 0.83583(13) 0.0652(4) Uani 1 1 d . . . . .
F1 F 0.2858(4) 0.9867(4) 0.4860(3) 0.0660(9) Uani 1 1 d . . . . .
F2 F 0.1138(4) 1.0600(3) 0.6202(3) 0.0608(8) Uani 1 1 d . . . . .
F3 F 0.9163(6) 0.9614(5) 0.7971(4) 0.1061(15) Uani 1 1 d . . . . .
F4 F 1.0170(4) 0.8232(5) 0.9190(4) 0.0930(13) Uani 1 1 d . . . . .
N1 N 0.3721(4) 0.5291(4) 0.6940(3) 0.0336(8) Uani 1 1 d . . . . .
N2 N 0.3743(5) 0.5760(4) 0.8163(3) 0.0344(8) Uani 1 1 d . . . . .
N3 N 0.2631(5) 0.4883(5) 0.5058(3) 0.0412(9) Uani 1 1 d . . . . .
N4 N 0.3558(5) 0.3589(4) 0.5221(3) 0.0422(9) Uani 1 1 d . . . . .
N5 N 0.4376(5) 0.7078(5) 1.0023(3) 0.0482(10) Uani 1 1 d . . . . .
N6 N 0.2920(6) 0.5975(5) 1.0001(4) 0.0537(11) Uani 1 1 d . . . . .
N7 N 0.1987(5) 0.7237(4) 0.6367(3) 0.0415(9) Uani 1 1 d . . . . .
N8 N 0.6109(5) 0.7796(5) 0.8520(3) 0.0442(9) 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 N4 1.282(5) . ?
C1 N1 1.379(5) . ?
C1 Cl1 1.680(4) . ?
C2 N3 1.287(6) . ?
C2 N7 1.359(6) . ?
C2 N1 1.395(5) . ?
C3 N7 1.489(5) . ?
C3 C4 1.507(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 F2 1.346(5) . ?
C4 F1 1.355(6) . ?
C4 C5 1.514(6) . ?
C5 N7 1.487(6) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 N6 1.285(6) . ?
C6 N2 1.373(6) . ?
C6 Cl2 1.691(5) . ?
C7 N5 1.310(6) . ?
C7 N8 1.353(6) . ?
C7 N2 1.377(5) . ?
C8 N8 1.497(7) . ?
C8 C9 1.521(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 F3 1.325(7) . ?
C9 F4 1.347(6) . ?
C9 C10 1.517(8) . ?
C10 N8 1.486(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N1 N2 1.364(5) . ?
N3 N4 1.414(5) . ?
N5 N6 1.418(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
N4 C1 N1 111.2(4) . . ?
N4 C1 Cl1 127.9(3) . . ?
N1 C1 Cl1 120.9(3) . . ?
N3 C2 N7 129.7(4) . . ?
N3 C2 N1 109.3(4) . . ?
N7 C2 N1 121.0(4) . . ?
N7 C3 C4 88.5(3) . . ?
N7 C3 H3A 113.9 . . ?
C4 C3 H3A 113.9 . . ?
N7 C3 H3B 113.9 . . ?
C4 C3 H3B 113.9 . . ?
H3A C3 H3B 111.1 . . ?
F2 C4 F1 104.9(3) . . ?
F2 C4 C5 115.4(4) . . ?
F1 C4 C5 114.8(4) . . ?
F2 C4 C3 116.8(4) . . ?
F1 C4 C3 114.6(4) . . ?
C5 C4 C3 90.5(3) . . ?
N7 C5 C4 88.3(3) . . ?
N7 C5 H5A 113.9 . . ?
C4 C5 H5A 113.9 . . ?
N7 C5 H5B 113.9 . . ?
C4 C5 H5B 113.9 . . ?
H5A C5 H5B 111.1 . . ?
N6 C6 N2 111.3(4) . . ?
N6 C6 Cl2 126.8(4) . . ?
N2 C6 Cl2 121.8(3) . . ?
N5 C7 N8 126.9(4) . . ?
N5 C7 N2 109.6(4) . . ?
N8 C7 N2 123.2(4) . . ?
N8 C8 C9 86.5(4) . . ?
N8 C8 H8A 114.2 . . ?
C9 C8 H8A 114.2 . . ?
N8 C8 H8B 114.2 . . ?
C9 C8 H8B 114.2 . . ?
H8A C8 H8B 111.4 . . ?
F3 C9 F4 106.0(5) . . ?
F3 C9 C10 114.7(5) . . ?
F4 C9 C10 116.1(5) . . ?
F3 C9 C8 114.8(5) . . ?
F4 C9 C8 114.7(5) . . ?
C10 C9 C8 90.5(4) . . ?
N8 C10 C9 87.0(3) . . ?
N8 C10 H10A 114.1 . . ?
C9 C10 H10A 114.1 . . ?
N8 C10 H10B 114.1 . . ?
C9 C10 H10B 114.1 . . ?
H10A C10 H10B 111.3 . . ?
N2 N1 C1 126.6(3) . . ?
N2 N1 C2 125.7(3) . . ?
C1 N1 C2 104.3(3) . . ?
N1 N2 C6 126.7(4) . . ?
N1 N2 C7 128.2(4) . . ?
C6 N2 C7 104.9(3) . . ?
C2 N3 N4 108.5(3) . . ?
C1 N4 N3 106.7(3) . . ?
C7 N5 N6 107.3(4) . . ?
C6 N6 N5 106.8(4) . . ?
C2 N7 C3 117.3(4) . . ?
C2 N7 C5 119.0(4) . . ?
C3 N7 C5 92.3(3) . . ?
C7 N8 C8 122.5(4) . . ?
C7 N8 C10 118.8(4) . . ?
C8 N8 C10 92.7(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N7 C3 C4 F2 -114.0(4) . . . . ?
N7 C3 C4 F1 122.8(4) . . . . ?
N7 C3 C4 C5 5.1(4) . . . . ?
F2 C4 C5 N7 115.1(4) . . . . ?
F1 C4 C5 N7 -122.6(4) . . . . ?
C3 C4 C5 N7 -5.1(4) . . . . ?
N8 C8 C9 F3 -104.1(5) . . . . ?
N8 C8 C9 F4 132.8(5) . . . . ?
N8 C8 C9 C10 13.5(4) . . . . ?
F3 C9 C10 N8 104.2(5) . . . . ?
F4 C9 C10 N8 -131.7(5) . . . . ?
C8 C9 C10 N8 -13.6(4) . . . . ?
N4 C1 N1 N2 161.3(4) . . . . ?
Cl1 C1 N1 N2 -20.0(6) . . . . ?
N4 C1 N1 C2 1.5(5) . . . . ?
Cl1 C1 N1 C2 -179.8(3) . . . . ?
N3 C2 N1 N2 -162.1(4) . . . . ?
N7 C2 N1 N2 18.0(6) . . . . ?
N3 C2 N1 C1 -2.1(5) . . . . ?
N7 C2 N1 C1 178.1(4) . . . . ?
C1 N1 N2 C6 -75.4(6) . . . . ?
C2 N1 N2 C6 80.3(5) . . . . ?
C1 N1 N2 C7 109.6(5) . . . . ?
C2 N1 N2 C7 -94.6(5) . . . . ?
N6 C6 N2 N1 -177.2(4) . . . . ?
Cl2 C6 N2 N1 5.4(6) . . . . ?
N6 C6 N2 C7 -1.3(5) . . . . ?
Cl2 C6 N2 C7 -178.7(3) . . . . ?
N5 C7 N2 N1 175.9(4) . . . . ?
N8 C7 N2 N1 1.2(6) . . . . ?
N5 C7 N2 C6 0.1(5) . . . . ?
N8 C7 N2 C6 -174.6(4) . . . . ?
N7 C2 N3 N4 -178.3(4) . . . . ?
N1 C2 N3 N4 1.9(5) . . . . ?
N1 C1 N4 N3 -0.4(5) . . . . ?
Cl1 C1 N4 N3 -179.0(3) . . . . ?
C2 N3 N4 C1 -0.9(5) . . . . ?
N8 C7 N5 N6 175.4(4) . . . . ?
N2 C7 N5 N6 1.0(5) . . . . ?
N2 C6 N6 N5 1.9(5) . . . . ?
Cl2 C6 N6 N5 179.1(3) . . . . ?
C7 N5 N6 C6 -1.8(5) . . . . ?
N3 C2 N7 C3 -2.1(7) . . . . ?
N1 C2 N7 C3 177.7(4) . . . . ?
N3 C2 N7 C5 -111.8(5) . . . . ?
N1 C2 N7 C5 68.0(5) . . . . ?
C4 C3 N7 C2 -129.7(4) . . . . ?
C4 C3 N7 C5 -5.2(4) . . . . ?
C4 C5 N7 C2 128.3(4) . . . . ?
C4 C5 N7 C3 5.2(4) . . . . ?
N5 C7 N8 C8 122.6(5) . . . . ?
N2 C7 N8 C8 -63.6(6) . . . . ?
N5 C7 N8 C10 8.3(7) . . . . ?
N2 C7 N8 C10 -177.9(4) . . . . ?
C9 C8 N8 C7 -140.7(4) . . . . ?
C9 C8 N8 C10 -13.8(4) . . . . ?
C9 C10 N8 C7 143.5(4) . . . . ?
C9 C10 N8 C8 13.9(4) . . . . ?

_refine_diff_density_max         0.322
_refine_diff_density_min         -0.371
_refine_diff_density_rms         0.087

