# Electronic Supplementary Material (ESI) for ChemComm.
# 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_090504_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1875001'
loop_
_audit_author_name
_audit_author_address
'Tian-Bing Ren'
;College of Chemistry and Chemical Engineering, Hunan University
China
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2018-10-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C8 H2 F3 N3'
_chemical_formula_sum            'C8 H0.12 F3 N3'
_chemical_formula_weight         195.24
_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'
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'
H H 0.0000 0.0000 '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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_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                   7.7891(11)
_cell_length_b                   9.8407(14)
_cell_length_c                   19.664(3)
_cell_angle_alpha                90
_cell_angle_beta                 90.909(5)
_cell_angle_gamma                90
_cell_volume                     1507.0(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    545
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      3.48
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.976
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6395
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1039 before and 0.0618 after correction. The Ratio of minimum to maximum transmission is 0.8576. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.721
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             769
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0567
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            7739
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.302
_diffrn_reflns_theta_min         3.336
_diffrn_ambient_temperature      273.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1227
_reflns_number_total             1882
_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       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.098
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1882
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1052
_refine_ls_R_factor_gt           0.0637
_refine_ls_restrained_S_all      1.098
_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)+(0.0356P)²+5.3520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1328
_refine_ls_wR_factor_ref         0.1512
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
2.a X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
F1 F -0.0538(2) 0.57765(19) 0.33186(9) 0.0300(5) Uani 1 1 d . . . . .
F2 F -0.0343(2) 0.80283(18) 0.41106(10) 0.0302(5) Uani 1 1 d . . . . .
F3 F 0.5508(2) 0.55291(18) 0.33387(9) 0.0292(5) Uani 1 1 d . . . . .
N1 N 0.2889(4) 1.0111(3) 0.48495(14) 0.0328(7) Uani 1 1 d . . . . .
N2 N 0.2401(4) 0.3456(3) 0.25757(14) 0.0341(7) Uani 1 1 d . . . . .
N3 N 0.5783(3) 0.7751(3) 0.41381(13) 0.0264(6) Uani 1 1 d . . . . .
H3A H 0.6688 0.7329 0.4010 0.032 Uiso 1 1 calc R . . . .
H3B H 0.5876 0.8461 0.4392 0.032 Uiso 1 1 calc R . . . .
C1 C 0.2742(4) 0.9145(3) 0.45268(15) 0.0223(6) Uani 1 1 d . . . . .
C2 C 0.2674(4) 0.7938(3) 0.41245(14) 0.0194(6) Uani 1 1 d . . . . .
C3 C 0.1096(4) 0.7410(3) 0.39117(14) 0.0210(6) Uani 1 1 d . . . . .
C4 C 0.0998(4) 0.6266(3) 0.35161(14) 0.0212(6) Uani 1 1 d . . . . .
C5 C 0.2498(4) 0.5612(3) 0.33197(14) 0.0203(6) Uani 1 1 d . . . . .
C6 C 0.2434(4) 0.4419(3) 0.29016(15) 0.0233(7) Uani 1 1 d . . . . .
C7 C 0.4215(4) 0.7300(3) 0.39419(14) 0.0195(6) Uani 1 1 d . . . . .
C8 C 0.4052(4) 0.6146(3) 0.35291(15) 0.0216(6) 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
F1 C4 1.342(3) . ?
F2 C3 1.339(3) . ?
F3 C8 1.345(3) . ?
N1 C1 1.147(4) . ?
N2 C6 1.144(4) . ?
N3 C7 1.350(4) . ?
C1 C2 1.428(4) . ?
C2 C3 1.392(4) . ?
C2 C7 1.406(4) . ?
C3 C4 1.369(4) . ?
C4 C5 1.394(4) . ?
C5 C6 1.434(4) . ?
C5 C8 1.376(4) . ?
C7 C8 1.401(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 C2 176.4(3) . . ?
C3 C2 C1 120.1(3) . . ?
C3 C2 C7 120.6(3) . . ?
C7 C2 C1 119.2(3) . . ?
F2 C3 C2 118.8(3) . . ?
F2 C3 C4 120.0(3) . . ?
C4 C3 C2 121.2(3) . . ?
F1 C4 C3 120.1(3) . . ?
F1 C4 C5 120.1(3) . . ?
C3 C4 C5 119.8(3) . . ?
C4 C5 C6 121.0(3) . . ?
C8 C5 C4 118.5(3) . . ?
C8 C5 C6 120.4(3) . . ?
N2 C6 C5 178.9(3) . . ?
N3 C7 C2 123.5(3) . . ?
N3 C7 C8 120.3(3) . . ?
C8 C7 C2 116.1(3) . . ?
F3 C8 C5 119.1(3) . . ?
F3 C8 C7 117.3(3) . . ?
C5 C8 C7 123.6(3) . . ?

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 C4 C5 C6 0.5(4) . . . . ?
F1 C4 C5 C8 179.7(3) . . . . ?
F2 C3 C4 F1 1.0(4) . . . . ?
F2 C3 C4 C5 -178.9(3) . . . . ?
N3 C7 C8 F3 -0.4(4) . . . . ?
N3 C7 C8 C5 178.7(3) . . . . ?
C1 C2 C3 F2 -2.2(4) . . . . ?
C1 C2 C3 C4 178.9(3) . . . . ?
C1 C2 C7 N3 1.4(4) . . . . ?
C1 C2 C7 C8 -178.0(3) . . . . ?
C2 C3 C4 F1 179.9(3) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C2 C7 C8 F3 179.0(2) . . . . ?
C2 C7 C8 C5 -1.8(4) . . . . ?
C3 C2 C7 N3 -179.2(3) . . . . ?
C3 C2 C7 C8 1.4(4) . . . . ?
C3 C4 C5 C6 -179.6(3) . . . . ?
C3 C4 C5 C8 -0.3(4) . . . . ?
C4 C5 C8 F3 -179.5(3) . . . . ?
C4 C5 C8 C7 1.3(4) . . . . ?
C6 C5 C8 F3 -0.3(4) . . . . ?
C6 C5 C8 C7 -179.5(3) . . . . ?
C7 C2 C3 F2 178.4(2) . . . . ?
C7 C2 C3 C4 -0.5(4) . . . . ?

_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_161208_s3_zg
_database_code_depnum_ccdc_archive 'CCDC 1875005'
loop_
_audit_author_name
_audit_author_address
'Tian-Bing Ren'
;College of Chemistry and Chemical Engineering, Hunan University
China
;
_audit_update_record             
;
2018-10-24 deposited with the CCDC.	2019-08-27 downloaded from the CCDC.
;
_audit_creation_date             2016-12-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H12 F2 N4'
_chemical_formula_sum            'C12 H12 F2 N4'
_chemical_formula_weight         250.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         c12h12n2f2
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'
F F 0.0171 0.0103 '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'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.3349(6)
_cell_length_b                   7.6871(4)
_cell_length_c                   12.6994(6)
_cell_angle_alpha                90
_cell_angle_beta                 96.325(5)
_cell_angle_gamma                90
_cell_volume                     1196.83(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1655
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5280
_cell_measurement_theta_min      3.5260
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77317
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.4
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4909
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         3.103
_diffrn_ambient_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.8554
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -40.00   27.00   1.0000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -14.9669   77.0000  -60.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega  -82.00    2.00   1.0000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -57.0000 -180.0000 84

#__ type_ start__ end____ width___ exp.time_
  3 omega  -14.00   12.00   1.0000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -64.00  -38.00   1.0000    3.2500
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000  -60.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0500792000
_diffrn_orient_matrix_UB_12      0.0458364000
_diffrn_orient_matrix_UB_13      0.0019822000
_diffrn_orient_matrix_UB_21      0.0102127000
_diffrn_orient_matrix_UB_22      -0.0174240000
_diffrn_orient_matrix_UB_23      0.0550448000
_diffrn_orient_matrix_UB_31      0.0271090000
_diffrn_orient_matrix_UB_32      -0.0781886000
_diffrn_orient_matrix_UB_33      -0.0110997000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1737
_reflns_number_total             2446
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         2446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0669
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.032
_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)+(0.0551P)²+0.2073P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1243
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2.a Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C)
;
_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
F1 F 0.44476(9) 0.83769(12) 0.42852(9) 0.0566(3) Uani 1 1 d . . . . .
F2 F 0.29993(9) 0.18482(12) 0.34073(8) 0.0544(3) Uani 1 1 d . . . . .
N1 N 0.35098(15) 0.7447(2) 0.65730(13) 0.0644(5) Uani 1 1 d . . . . .
N2 N 0.26682(13) 0.33219(19) 0.53958(13) 0.0521(4) Uani 1 1 d . . . . .
N3 N 0.38592(16) 0.2837(2) 0.10817(14) 0.0660(5) Uani 1 1 d . . . . .
N4 N 0.47210(13) 0.6964(2) 0.22738(13) 0.0540(4) Uani 1 1 d . . . . .
C1 C 0.40745(13) 0.6765(2) 0.40233(13) 0.0380(4) Uani 1 1 d . . . . .
C2 C 0.35683(12) 0.5883(2) 0.47865(12) 0.0368(4) Uani 1 1 d . . . . .
C3 C 0.31845(12) 0.4174(2) 0.46305(13) 0.0366(4) Uani 1 1 d . . . . .
C4 C 0.33727(13) 0.3461(2) 0.36624(13) 0.0378(4) Uani 1 1 d . . . . .
C5 C 0.38678(12) 0.4349(2) 0.28929(12) 0.0365(4) Uani 1 1 d . . . . .
C6 C 0.42505(12) 0.6068(2) 0.30544(13) 0.0371(4) Uani 1 1 d . . . . .
C7 C 0.35212(14) 0.6747(2) 0.57846(14) 0.0450(4) Uani 1 1 d . . . . .
C8 C 0.38809(14) 0.3511(2) 0.18827(14) 0.0450(4) Uani 1 1 d . . . . .
C9 C 0.17342(15) 0.4099(3) 0.57989(15) 0.0605(6) Uani 1 1 d . . . . .
H9A H 0.1627 0.5253 0.5517 0.091 Uiso 1 1 calc GR . . . .
H9B H 0.1855 0.4154 0.6558 0.091 Uiso 1 1 calc GR . . . .
H9C H 0.1098 0.3409 0.5590 0.091 Uiso 1 1 calc GR . . . .
C10 C 0.27656(18) 0.1454(2) 0.55414(17) 0.0606(6) Uani 1 1 d . . . . .
H10A H 0.2180 0.0883 0.5114 0.091 Uiso 1 1 calc GR . . . .
H10B H 0.2731 0.1174 0.6274 0.091 Uiso 1 1 calc GR . . . .
H10C H 0.3451 0.1068 0.5332 0.091 Uiso 1 1 calc GR . . . .
C11 C 0.56203(16) 0.6232(3) 0.17943(16) 0.0620(6) Uani 1 1 d . . . . .
H11A H 0.6281 0.6820 0.2058 0.093 Uiso 1 1 calc GR . . . .
H11B H 0.5495 0.6369 0.1039 0.093 Uiso 1 1 calc GR . . . .
H11C H 0.5685 0.5017 0.1965 0.093 Uiso 1 1 calc GR . . . .
C12 C 0.45709(17) 0.8829(2) 0.21486(16) 0.0576(5) Uani 1 1 d . . . . .
H12A H 0.3886 0.9159 0.2382 0.086 Uiso 1 1 calc GR . . . .
H12B H 0.4575 0.9134 0.1416 0.086 Uiso 1 1 calc GR . . . .
H12C H 0.5153 0.9426 0.2565 0.086 Uiso 1 1 calc GR . . . .


_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
F1 C1 1.3508(17) . ?
F2 C4 1.3497(18) . ?
N1 C7 1.138(2) . ?
N2 C3 1.384(2) . ?
N2 C9 1.441(2) . ?
N2 C10 1.451(2) . ?
N3 C8 1.139(2) . ?
N4 C6 1.386(2) . ?
N4 C11 1.438(2) . ?
N4 C12 1.452(2) . ?
C1 C2 1.386(2) . ?
C1 C6 1.381(2) . ?
C2 C3 1.402(2) . ?
C2 C7 1.438(2) . ?
C3 C4 1.389(2) . ?
C4 C5 1.388(2) . ?
C5 C6 1.411(2) . ?
C5 C8 1.437(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

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
C3 N2 C9 120.06(15) . . ?
C3 N2 C10 121.33(14) . . ?
C9 N2 C10 115.04(15) . . ?
C6 N4 C11 120.80(15) . . ?
C6 N4 C12 120.69(15) . . ?
C11 N4 C12 115.80(15) . . ?
F1 C1 C2 116.36(14) . . ?
F1 C1 C6 119.50(14) . . ?
C6 C1 C2 124.08(15) . . ?
C1 C2 C3 122.01(15) . . ?
C1 C2 C7 117.07(15) . . ?
C3 C2 C7 120.77(15) . . ?
N2 C3 C2 121.22(15) . . ?
N2 C3 C4 124.70(15) . . ?
C4 C3 C2 114.07(14) . . ?
F2 C4 C3 119.29(14) . . ?
F2 C4 C5 116.60(14) . . ?
C5 C4 C3 123.97(15) . . ?
C4 C5 C6 121.64(15) . . ?
C4 C5 C8 117.22(15) . . ?
C6 C5 C8 120.87(15) . . ?
N4 C6 C5 121.41(15) . . ?
C1 C6 N4 124.34(15) . . ?
C1 C6 C5 114.20(14) . . ?
N1 C7 C2 178.3(2) . . ?
N3 C8 C5 178.0(2) . . ?
N2 C9 H9A 109.5 . . ?
N2 C9 H9B 109.5 . . ?
N2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N2 C10 H10A 109.5 . . ?
N2 C10 H10B 109.5 . . ?
N2 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C11 H11A 109.5 . . ?
N4 C11 H11B 109.5 . . ?
N4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N4 C12 H12A 109.5 . . ?
N4 C12 H12B 109.5 . . ?
N4 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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 C1 C2 C3 -177.39(14) . . . . ?
F1 C1 C2 C7 -1.8(2) . . . . ?
F1 C1 C6 N4 -5.2(2) . . . . ?
F1 C1 C6 C5 177.22(13) . . . . ?
F2 C4 C5 C6 177.48(14) . . . . ?
F2 C4 C5 C8 3.4(2) . . . . ?
N2 C3 C4 F2 2.7(2) . . . . ?
N2 C3 C4 C5 178.35(15) . . . . ?
C1 C2 C3 N2 -179.14(15) . . . . ?
C1 C2 C3 C4 0.9(2) . . . . ?
C2 C1 C6 N4 177.61(15) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
C2 C3 C4 F2 -177.35(13) . . . . ?
C2 C3 C4 C5 -1.7(2) . . . . ?
C3 C4 C5 C6 1.7(2) . . . . ?
C3 C4 C5 C8 -172.36(15) . . . . ?
C4 C5 C6 N4 -178.45(15) . . . . ?
C4 C5 C6 C1 -0.8(2) . . . . ?
C6 C1 C2 C3 -0.1(3) . . . . ?
C6 C1 C2 C7 175.49(15) . . . . ?
C7 C2 C3 N2 5.4(2) . . . . ?
C7 C2 C3 C4 -174.54(14) . . . . ?
C8 C5 C6 N4 -4.6(2) . . . . ?
C8 C5 C6 C1 173.09(15) . . . . ?
C9 N2 C3 C2 54.7(2) . . . . ?
C9 N2 C3 C4 -125.31(19) . . . . ?
C10 N2 C3 C2 -147.64(18) . . . . ?
C10 N2 C3 C4 32.3(3) . . . . ?
C11 N4 C6 C1 128.8(2) . . . . ?
C11 N4 C6 C5 -53.7(2) . . . . ?
C12 N4 C6 C1 -31.7(3) . . . . ?
C12 N4 C6 C5 145.72(18) . . . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
