# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2014

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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 1023883'
_audit_update_record             
;
2014-09-11 deposited with the CCDC.
2014-11-21 downloaded from the CCDC.
;


#=============================================================================
_audit_creation_method           'SHELXL-2014/6, manual editing plus enCIFer'
_audit_creation_date             '11 September 2014'
#=============================================================================

#=============================================================================
# GENERAL AND CHEMICAL DATA
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 F N3'
_chemical_formula_sum            'C10 H8 F N3'
_chemical_formula_weight         189.19

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'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_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                   6.4282(18)
_cell_length_b                   8.584(2)
_cell_length_c                   8.968(3)
_cell_angle_alpha                108.015(10)
_cell_angle_beta                 103.788(10)
_cell_angle_gamma                92.762(10)
_cell_volume                     453.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3458
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      24.85

_exptl_crystal_description       Block
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_F_000             196
_exptl_transmission_factor_min   0.2161
_exptl_transmission_factor_max   0.2544
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
 SADABS V2012/1 (Bruker AXS Inc.) 
;

#==============================================================================
# EXPERIMENTAL DATA
#============================================================================== 

_diffrn_ambient_temperature      150(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 X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13052
_diffrn_reflns_av_unetI/netI     0.0748
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.554
_diffrn_reflns_theta_max         25.342
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.985
_reflns_number_total             1636
_reflns_number_gt                891
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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       'APEX2 2012.4 (Bruker AXS Inc., 2012)'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'

_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)+(0.0341P)²+0.3185P] 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         1636
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1285
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1244
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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 0.1710(3) 0.8931(2) 0.5089(2) 0.0409(5) Uani 1 1 d . . . . .
N1 N 0.6007(4) 0.9347(3) 0.7078(3) 0.0334(7) Uani 1 1 d . . . . .
N2 N 0.8364(5) 0.3605(3) 0.2499(3) 0.0441(8) Uani 1 1 d . . . . .
N3 N 0.2327(5) 0.3343(3) -0.0305(3) 0.0436(7) Uani 1 1 d . . . . .
C1 C 0.4628(5) 1.0363(4) 0.7956(4) 0.0407(9) Uani 1 1 d . . . . .
H1A H 0.3998 1.1086 0.7361 0.061 Uiso 1 1 calc R U . . .
H1B H 0.5494 1.1037 0.9046 0.061 Uiso 1 1 calc R U . . .
H1C H 0.3467 0.9644 0.8048 0.061 Uiso 1 1 calc R U . . .
C2 C 0.8288(5) 0.9559(4) 0.7940(4) 0.0410(9) Uani 1 1 d . . . . .
H2A H 0.8562 0.8674 0.8409 0.061 Uiso 1 1 calc R U . . .
H2B H 0.8663 1.0632 0.8811 0.061 Uiso 1 1 calc R U . . .
H2C H 0.9171 0.9513 0.7178 0.061 Uiso 1 1 calc R U . . .
C3 C 0.5239(5) 0.8115(3) 0.5625(3) 0.0275(7) Uani 1 1 d . . . . .
C4 C 0.3131(5) 0.7883(4) 0.4609(4) 0.0289(7) Uani 1 1 d . . . . .
C5 C 0.2374(5) 0.6692(3) 0.3127(3) 0.0302(8) Uani 1 1 d . . . . .
H5 H 0.0931 0.6618 0.2503 0.036 Uiso 1 1 calc R U . . .
C6 C 0.3737(5) 0.5580(3) 0.2528(3) 0.0279(8) Uani 1 1 d . . . . .
C7 C 0.5834(5) 0.5731(3) 0.3494(3) 0.0268(7) Uani 1 1 d . . . . .
C8 C 0.6588(5) 0.6965(3) 0.5008(3) 0.0293(8) Uani 1 1 d . . . . .
H8 H 0.8028 0.7035 0.5634 0.035 Uiso 1 1 calc R U . . .
C9 C 0.2963(5) 0.4335(4) 0.0959(4) 0.0326(8) Uani 1 1 d . . . . .
C10 C 0.7259(5) 0.4561(4) 0.2934(4) 0.0310(8) 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.
;


#=============================================================================
# GEOMETRY
#============================================================================= 

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 1.362(3) . ?
N1 C3 1.360(4) . ?
N1 C2 1.458(4) . ?
N1 C1 1.466(4) . ?
N2 C10 1.149(4) . ?
N3 C9 1.152(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.407(4) . ?
C3 C8 1.416(4) . ?
C4 C5 1.361(4) . ?
C5 C6 1.398(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.394(4) . ?
C6 C9 1.433(4) . ?
C7 C8 1.395(4) . ?
C7 C10 1.448(4) . ?
C8 H8 0.9500 . ?

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 N1 C2 119.3(3) . . ?
C3 N1 C1 123.8(3) . . ?
C2 N1 C1 116.4(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C4 124.6(3) . . ?
N1 C3 C8 120.7(3) . . ?
C4 C3 C8 114.7(3) . . ?
C5 C4 F1 115.7(3) . . ?
C5 C4 C3 125.0(3) . . ?
F1 C4 C3 119.3(3) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 118.1(3) . . ?
C7 C6 C9 122.0(3) . . ?
C5 C6 C9 119.9(3) . . ?
C6 C7 C8 121.7(3) . . ?
C6 C7 C10 119.4(3) . . ?
C8 C7 C10 119.0(3) . . ?
C7 C8 C3 121.1(3) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
N3 C9 C6 179.4(4) . . ?
N2 C10 C7 178.4(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
C2 N1 C3 C4 -173.7(3) . . . . ?
C1 N1 C3 C4 14.6(4) . . . . ?
C2 N1 C3 C8 4.9(4) . . . . ?
C1 N1 C3 C8 -166.8(3) . . . . ?
N1 C3 C4 C5 177.4(3) . . . . ?
C8 C3 C4 C5 -1.3(4) . . . . ?
N1 C3 C4 F1 -1.0(4) . . . . ?
C8 C3 C4 F1 -179.6(2) . . . . ?
F1 C4 C5 C6 179.0(2) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 C7 0.5(4) . . . . ?
C4 C5 C6 C9 -179.2(3) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C9 C6 C7 C8 178.8(3) . . . . ?
C5 C6 C7 C10 177.8(3) . . . . ?
C9 C6 C7 C10 -2.5(4) . . . . ?
C6 C7 C8 C3 0.1(4) . . . . ?
C10 C7 C8 C3 -178.5(2) . . . . ?
N1 C3 C8 C7 -177.8(3) . . . . ?
C4 C3 C8 C7 0.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C5 H5 N3 0.95 2.52 3.440(4) 163.0 2_565

_refine_diff_density_max         0.182
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.050
_shelxl_version_number           2014/6


#=============================================================================
#   SHELXL Ins File
#=============================================================================

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_2
_database_code_depnum_ccdc_archive 'CCDC 1023884'
_audit_update_record             
;
2014-09-11 deposited with the CCDC.
2014-11-21 downloaded from the CCDC.
;


#=============================================================================
_audit_creation_method           'SHELXL-2014/6, manual editing plus enCIFer'
_audit_creation_date             '11 September 2014'
#=============================================================================

#=============================================================================
# GENERAL AND CHEMICAL DATA
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 Cl N3'
_chemical_formula_sum            'C10 H8 Cl N3'
_chemical_formula_weight         205.64

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_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                   7.0606(4)
_cell_length_b                   7.0918(4)
_cell_length_c                   10.4983(6)
_cell_angle_alpha                76.075(3)
_cell_angle_beta                 71.330(3)
_cell_angle_gamma                77.999(3)
_cell_volume                     478.45(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6964
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      29.49

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             212
_exptl_transmission_factor_min   0.7022
_exptl_transmission_factor_max   0.7457
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.358
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
 SADABS V2012/1 (Bruker AXS Inc.) 
;

#==============================================================================
# EXPERIMENTAL DATA
#============================================================================== 

_diffrn_ambient_temperature      150(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 X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16051
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.761
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2568
_reflns_number_gt                2113
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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       'APEX2 2012.4 (Bruker AXS Inc., 2012)'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'

_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)+(0.0409P)²+0.1327P] 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         2568
_refine_ls_number_parameters     129
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0345
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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 0.17458(5) 0.43464(5) 0.25807(3) 0.03024(12) Uani 1 1 d . . . . .
N1 N 0.62945(16) 0.26618(17) 0.14685(11) 0.0248(2) Uani 1 1 d . . . . .
C1 C 0.8481(2) 0.2467(2) 0.08560(14) 0.0306(3) Uani 1 1 d . . . . .
H1A H 0.9044 0.3358 0.1175 0.046 Uiso 1 1 calc R U . . .
H1B H 0.8784 0.2800 -0.0143 0.046 Uiso 1 1 calc R U . . .
H1C H 0.9083 0.1112 0.1126 0.046 Uiso 1 1 calc R U . . .
C2 C 0.5190(2) 0.2127(2) 0.06742(14) 0.0307(3) Uani 1 1 d . . . . .
H2A H 0.3991 0.1570 0.1297 0.046 Uiso 1 1 calc R U . . .
H2B H 0.6064 0.1153 0.0139 0.046 Uiso 1 1 calc R U . . .
H2C H 0.4776 0.3299 0.0054 0.046 Uiso 1 1 calc R U . . .
N2 N 0.26961(19) 0.2664(2) 0.83019(12) 0.0346(3) Uani 1 1 d . . . . .
N3 N 0.86116(18) 0.09684(19) 0.65644(13) 0.0314(3) Uani 1 1 d . . . . .
C3 C 0.55354(18) 0.26760(17) 0.28361(12) 0.0198(2) Uani 1 1 d . . . . .
C4 C 0.34845(18) 0.33090(18) 0.34956(13) 0.0210(3) Uani 1 1 d . . . . .
C5 C 0.27793(18) 0.32682(18) 0.48862(13) 0.0214(3) Uani 1 1 d . . . . .
H5 H 0.1384 0.3658 0.5290 0.026 Uiso 1 1 calc R U . . .
C7 C 0.61327(18) 0.21007(17) 0.50793(13) 0.0195(2) Uani 1 1 d . . . . .
C6 C 0.40798(18) 0.26645(17) 0.57072(13) 0.0201(2) Uani 1 1 d . . . . .
C8 C 0.68372(18) 0.21027(17) 0.36898(13) 0.0209(3) Uani 1 1 d . . . . .
H8 H 0.8235 0.1708 0.3295 0.025 Uiso 1 1 calc R U . . .
C9 C 0.33171(19) 0.26601(19) 0.71482(14) 0.0239(3) Uani 1 1 d . . . . .
C10 C 0.75275(19) 0.14686(18) 0.58992(13) 0.0227(3) 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.
;


#=============================================================================
# GEOMETRY
#============================================================================= 

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 C4 1.7350(12) . ?
N1 C3 1.3642(16) . ?
N1 C1 1.4613(17) . ?
N1 C2 1.4623(17) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
N2 C9 1.1491(18) . ?
N3 C10 1.1443(18) . ?
C3 C8 1.4177(17) . ?
C3 C4 1.4196(17) . ?
C4 C5 1.3786(18) . ?
C5 C6 1.3910(17) . ?
C5 H5 0.9500 . ?
C7 C8 1.3821(17) . ?
C7 C6 1.4033(17) . ?
C7 C10 1.4440(17) . ?
C6 C9 1.4337(18) . ?
C8 H8 0.9500 . ?

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 N1 C1 118.88(11) . . ?
C3 N1 C2 123.16(11) . . ?
C1 N1 C2 114.32(11) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 C8 120.03(11) . . ?
N1 C3 C4 124.40(11) . . ?
C8 C3 C4 115.53(11) . . ?
C5 C4 C3 122.34(11) . . ?
C5 C4 Cl1 115.68(9) . . ?
C3 C4 Cl1 121.83(10) . . ?
C4 C5 C6 121.00(11) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C8 C7 C6 121.02(11) . . ?
C8 C7 C10 119.33(11) . . ?
C6 C7 C10 119.64(11) . . ?
C5 C6 C7 118.11(11) . . ?
C5 C6 C9 120.02(11) . . ?
C7 C6 C9 121.87(11) . . ?
C7 C8 C3 121.92(11) . . ?
C7 C8 H8 119.0 . . ?
C3 C8 H8 119.0 . . ?
N2 C9 C6 179.60(15) . . ?
N3 C10 C7 179.08(14) . . ?

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
C1 N1 C3 C8 -13.07(18) . . . . ?
C2 N1 C3 C8 144.16(12) . . . . ?
C1 N1 C3 C4 164.43(12) . . . . ?
C2 N1 C3 C4 -38.34(19) . . . . ?
N1 C3 C4 C5 178.97(12) . . . . ?
C8 C3 C4 C5 -3.43(17) . . . . ?
N1 C3 C4 Cl1 -5.70(17) . . . . ?
C8 C3 C4 Cl1 171.90(9) . . . . ?
C3 C4 C5 C6 2.42(19) . . . . ?
Cl1 C4 C5 C6 -173.19(9) . . . . ?
C4 C5 C6 C7 0.11(18) . . . . ?
C4 C5 C6 C9 179.13(11) . . . . ?
C8 C7 C6 C5 -1.41(18) . . . . ?
C10 C7 C6 C5 179.90(11) . . . . ?
C8 C7 C6 C9 179.58(11) . . . . ?
C10 C7 C6 C9 0.90(18) . . . . ?
C6 C7 C8 C3 0.24(19) . . . . ?
C10 C7 C8 C3 178.93(11) . . . . ?
N1 C3 C8 C7 179.82(11) . . . . ?
C4 C3 C8 C7 2.10(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B Cl1 0.98 2.93 3.8008(15) 148.5 2_665
C8 H8 N3 0.95 2.63 3.4585(17) 146.4 2_756

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.049
_shelxl_version_number           2014/6


#=============================================================================
#   SHELXL Ins File
#=============================================================================

####################################################################### 
# 
# 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/. 
# 
# Audit and citation data items have may 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_3
_database_code_depnum_ccdc_archive 'CCDC 1023885'
_audit_update_record             
;
2014-09-11 deposited with the CCDC.
2014-11-21 downloaded from the CCDC.
;


#=============================================================================
_audit_creation_method           'SHELXL-2014/6, manual editing plus enCIFer'
_audit_creation_date             '11 September 2014'
#=============================================================================

#=============================================================================
# GENERAL AND CHEMICAL DATA
#=============================================================================

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 F2 N4'
_chemical_formula_sum            'C12 H12 F2 N4'
_chemical_formula_weight         250.26

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'

#=============================================================================
# CRYSTAL DATA
#=============================================================================

_space_group_crystal_system      Monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.7161(18)
_cell_length_b                   16.551(5)
_cell_length_c                   11.136(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.593(10)
_cell_angle_gamma                90
_cell_volume                     1236.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1435
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      21.61

_exptl_crystal_description       Needle
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             520
_exptl_transmission_factor_min   0.6535
_exptl_transmission_factor_max   0.7452
_exptl_crystal_size_max          0.080
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.992
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   
; 
 SADABS V2012/1 (Bruker AXS Inc.) 
;

#==============================================================================
# EXPERIMENTAL DATA
#============================================================================== 

_diffrn_ambient_temperature      150(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 X8 Kappa CCD APEX II'
_diffrn_measurement_method       'ω / φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8683
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_av_R_equivalents  0.0661
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.617
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2250
_reflns_number_gt                1164
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .


#=============================================================================
# REFINEMENT DATA
#=============================================================================

_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       'APEX2 2012.4 (Bruker AXS Inc., 2012)'
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 2009)'
_computing_publication_material  'SHELXTL (Sheldrick, 2014)'

_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)+(0.0832P)²+0.1888P] 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         2250
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1423
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1771
_refine_ls_wR_factor_gt          0.1413
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000


#=============================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS
#=============================================================================

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 0.2628(3) 0.30142(13) 0.59446(18) 0.0527(6) Uani 1 1 d . . . . .
F2 F 0.2628(3) 0.55268(12) 0.28563(18) 0.0494(6) Uani 1 1 d . . . . .
N1 N 0.2964(5) 0.39752(19) 0.1899(3) 0.0505(9) Uani 1 1 d . . . . .
N2 N 0.2769(5) 0.26667(17) 0.3526(3) 0.0512(9) Uani 1 1 d . . . . .
N3 N 0.2462(6) 0.4641(2) 0.7898(4) 0.0688(11) Uani 1 1 d . . . . .
N4 N 0.2168(5) 0.6513(2) 0.5536(3) 0.0576(10) Uani 1 1 d . . . . .
C1 C 0.2114(7) 0.4512(3) 0.0981(4) 0.0644(12) Uani 1 1 d . . . . .
H1A H 0.3023 0.4965 0.0865 0.097 Uiso 1 1 calc R U . . .
H1B H 0.0830 0.4717 0.1234 0.097 Uiso 1 1 calc R U . . .
H1C H 0.1914 0.4215 0.0224 0.097 Uiso 1 1 calc R U . . .
C2 C 0.4667(7) 0.3502(3) 0.1509(4) 0.0670(13) Uani 1 1 d . . . . .
H2A H 0.5250 0.3197 0.2193 0.101 Uiso 1 1 calc R U . . .
H2B H 0.5672 0.3867 0.1199 0.101 Uiso 1 1 calc R U . . .
H2C H 0.4217 0.3125 0.0874 0.101 Uiso 1 1 calc R U . . .
C3 C 0.1252(6) 0.2405(2) 0.2637(4) 0.0604(12) Uani 1 1 d . . . . .
H3A H 0.0474 0.2874 0.2350 0.091 Uiso 1 1 calc R U . . .
H3B H 0.0366 0.2014 0.3002 0.091 Uiso 1 1 calc R U . . .
H3C H 0.1893 0.2152 0.1959 0.091 Uiso 1 1 calc R U . . .
C4 C 0.3913(6) 0.2033(2) 0.4133(4) 0.0596(12) Uani 1 1 d . . . . .
H4A H 0.3033 0.1709 0.4619 0.089 Uiso 1 1 calc R U . . .
H4B H 0.4966 0.2275 0.4654 0.089 Uiso 1 1 calc R U . . .
H4C H 0.4516 0.1686 0.3534 0.089 Uiso 1 1 calc R U . . .
C5 C 0.2779(5) 0.4110(2) 0.3107(3) 0.0387(9) Uani 1 1 d . . . . .
C6 C 0.2767(5) 0.3450(2) 0.3929(3) 0.0400(9) Uani 1 1 d . . . . .
C7 C 0.2709(5) 0.3631(2) 0.5149(3) 0.0394(9) Uani 1 1 d . . . . .
C8 C 0.2596(5) 0.4398(2) 0.5612(3) 0.0372(9) Uani 1 1 d . . . . .
C9 C 0.2475(5) 0.5043(2) 0.4800(3) 0.0357(8) Uani 1 1 d . . . . .
C10 C 0.2582(5) 0.4881(2) 0.3596(3) 0.0368(9) Uani 1 1 d . . . . .
C11 C 0.2519(6) 0.4528(2) 0.6879(4) 0.0482(10) Uani 1 1 d . . . . .
C12 C 0.2315(5) 0.5861(2) 0.5206(3) 0.0420(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.
;

#=============================================================================
# GEOMETRY
#============================================================================= 

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 C7 1.354(4) . ?
F2 C10 1.350(4) . ?
N1 C5 1.375(4) . ?
N1 C1 1.451(5) . ?
N1 C2 1.469(5) . ?
N2 C6 1.371(4) . ?
N2 C4 1.449(5) . ?
N2 C3 1.454(5) . ?
N3 C11 1.153(5) . ?
N4 C12 1.144(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C10 1.396(5) . ?
C5 C6 1.426(5) . ?
C6 C7 1.394(5) . ?
C7 C8 1.373(5) . ?
C8 C9 1.398(5) . ?
C8 C11 1.431(5) . ?
C9 C10 1.372(5) . ?
C9 C12 1.434(5) . ?

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
C5 N1 C1 122.7(3) . . ?
C5 N1 C2 118.8(3) . . ?
C1 N1 C2 113.9(3) . . ?
C6 N2 C4 122.7(3) . . ?
C6 N2 C3 119.5(3) . . ?
C4 N2 C3 116.3(3) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N2 C3 H3A 109.5 . . ?
N2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
N2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 H4A 109.5 . . ?
N2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
N2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C10 123.0(3) . . ?
N1 C5 C6 120.5(3) . . ?
C10 C5 C6 116.5(3) . . ?
N2 C6 C7 121.5(3) . . ?
N2 C6 C5 120.9(3) . . ?
C7 C6 C5 117.5(3) . . ?
F1 C7 C8 116.6(3) . . ?
F1 C7 C6 118.6(3) . . ?
C8 C7 C6 124.7(3) . . ?
C7 C8 C9 117.8(3) . . ?
C7 C8 C11 120.9(3) . . ?
C9 C8 C11 121.3(3) . . ?
C10 C9 C8 118.6(3) . . ?
C10 C9 C12 120.0(3) . . ?
C8 C9 C12 121.4(3) . . ?
F2 C10 C9 116.5(3) . . ?
F2 C10 C5 118.7(3) . . ?
C9 C10 C5 124.7(3) . . ?
N3 C11 C8 179.3(4) . . ?
N4 C12 C9 179.2(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
C1 N1 C5 C10 -28.7(6) . . . . ?
C2 N1 C5 C10 125.8(4) . . . . ?
C1 N1 C5 C6 150.9(4) . . . . ?
C2 N1 C5 C6 -54.7(5) . . . . ?
C4 N2 C6 C7 -40.8(5) . . . . ?
C3 N2 C6 C7 124.6(4) . . . . ?
C4 N2 C6 C5 140.6(4) . . . . ?
C3 N2 C6 C5 -54.0(5) . . . . ?
N1 C5 C6 N2 -5.6(5) . . . . ?
C10 C5 C6 N2 174.0(3) . . . . ?
N1 C5 C6 C7 175.8(3) . . . . ?
C10 C5 C6 C7 -4.6(5) . . . . ?
N2 C6 C7 F1 -0.8(5) . . . . ?
C5 C6 C7 F1 177.8(3) . . . . ?
N2 C6 C7 C8 -176.3(3) . . . . ?
C5 C6 C7 C8 2.3(5) . . . . ?
F1 C7 C8 C9 -173.7(3) . . . . ?
C6 C7 C8 C9 1.9(5) . . . . ?
F1 C7 C8 C11 3.6(5) . . . . ?
C6 C7 C8 C11 179.2(3) . . . . ?
C7 C8 C9 C10 -3.4(5) . . . . ?
C11 C8 C9 C10 179.2(3) . . . . ?
C7 C8 C9 C12 178.8(3) . . . . ?
C11 C8 C9 C12 1.5(5) . . . . ?
C8 C9 C10 F2 -174.6(3) . . . . ?
C12 C9 C10 F2 3.2(5) . . . . ?
C8 C9 C10 C5 0.9(5) . . . . ?
C12 C9 C10 C5 178.7(3) . . . . ?
N1 C5 C10 F2 -1.9(5) . . . . ?
C6 C5 C10 F2 178.6(3) . . . . ?
N1 C5 C10 C9 -177.2(3) . . . . ?
C6 C5 C10 C9 3.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1B N3 0.98 2.67 3.649(6) 174.1 3_566
C2 H2A N2 0.98 2.44 2.974(6) 113.4 .

_refine_diff_density_max         0.241
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.053
_shelxl_version_number           2014/6


#=============================================================================
#   SHELXL Ins File
#=============================================================================

