# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_DB10
_database_code_depnum_ccdc_archive 'CCDC 982077'
_audit_update_record             
;
2016-08-24 deposited with the CCDC.
2016-11-16 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            'C13 H11 F N2'
_chemical_formula_weight         214.24

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.5078(9)
_cell_length_b                   8.3906(6)
_cell_length_c                   11.3259(9)
_cell_angle_alpha                90
_cell_angle_beta                 116.232(4)
_cell_angle_gamma                90
_cell_volume                     1066.21(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9468
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      30.53

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_F_000             448
_exptl_transmission_factor_min   6.758
_exptl_transmission_factor_max   7.049
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   0.982
_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
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8359
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0455
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.815
_diffrn_reflns_theta_max         27.462
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2361
_reflns_number_gt                1725
_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)+(0.0658P)²+0.2692P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2361
_refine_ls_number_parameters     150
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1388
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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
N2 N -0.03904(13) 0.38590(19) 0.25508(16) 0.0267(4) Uani 1 1 d . . . . .
H2A H -0.0829 0.4639 0.2052 0.032 Uiso 1 1 calc R U . . .
H2B H -0.0690 0.2894 0.2466 0.032 Uiso 1 1 calc R U . . .
N1 N 0.12021(13) 0.55501(18) 0.35887(15) 0.0238(4) Uani 1 1 d . . . . .
F1A F 0.27378(16) 0.2761(2) 0.33394(19) 0.0300(4) Uani 0.5577(18) 1 d . . P A 1
C1A C 0.13852(15) 0.2703(2) 0.42008(17) 0.0213(4) Uani 0.5577(18) 1 d . . P A 1
C2A C 0.23665(15) 0.2078(2) 0.40874(19) 0.0255(4) Uani 0.5577(18) 1 d . . P A 1
C3A C 0.29585(16) 0.0749(2) 0.4768(2) 0.0293(4) Uani 0.5577(18) 1 d . . P A 1
H3A H 0.3625 0.0351 0.4668 0.035 Uiso 0.5577(18) 1 calc R U P A 1
C4A C 0.25805(17) -0.0006(2) 0.55999(19) 0.0301(4) Uani 0.5577(18) 1 d . . P A
1
H4A H 0.2989 -0.0926 0.6075 0.036 Uiso 0.5577(18) 1 calc R U P A 1
C5A C 0.16067(18) 0.0572(2) 0.57434(19) 0.0302(5) Uani 0.5577(18) 1 d . . P A 1
H5A H 0.1342 0.0056 0.6313 0.036 Uiso 0.5577(18) 1 calc R U P A 1
C6A C 0.10259(16) 0.1915(2) 0.50441(18) 0.0267(4) Uani 0.5577(18) 1 d . . P A 1
H6A H 0.0359 0.2312 0.5144 0.032 Uiso 0.5577(18) 1 calc R U P A 1
F1B F 0.0205(2) 0.2530(3) 0.5254(2) 0.0300(4) Uani 0.4423(18) 1 d . . P A 2
C1B C 0.13852(15) 0.2703(2) 0.42008(17) 0.0213(4) Uani 0.4423(18) 1 d . . P A 2
C2B C 0.10259(16) 0.1915(2) 0.50441(18) 0.0267(4) Uani 0.4423(18) 1 d . . P A 2
C3B C 0.16067(18) 0.0572(2) 0.57434(19) 0.0302(5) Uani 0.4423(18) 1 d . . P A 2
H3B H 0.1342 0.0056 0.6313 0.036 Uiso 0.4423(18) 1 calc R U P A 2
C4B C 0.25805(17) -0.0006(2) 0.55999(19) 0.0301(4) Uani 0.4423(18) 1 d . . P A
2
H4B H 0.2989 -0.0926 0.6075 0.036 Uiso 0.4423(18) 1 calc R U P A 2
C5B C 0.29585(16) 0.0749(2) 0.4768(2) 0.0293(4) Uani 0.4423(18) 1 d . . P A 2
H5B H 0.3625 0.0351 0.4668 0.035 Uiso 0.4423(18) 1 calc R U P A 2
C6B C 0.23665(15) 0.2078(2) 0.40874(19) 0.0255(4) Uani 0.4423(18) 1 d . . P A 2
H6B H 0.2635 0.2590 0.3519 0.031 Uiso 0.4423(18) 1 calc R U P A 2
C7 C 0.23639(15) 0.5826(2) 0.46048(18) 0.0222(4) Uani 1 1 d . . . . .
C8 C 0.32221(15) 0.6449(2) 0.42582(18) 0.0252(4) Uani 1 1 d . . . . .
H8 H 0.3018 0.6664 0.3360 0.030 Uiso 1 1 calc R U . . .
C9 C 0.43610(16) 0.6753(2) 0.5206(2) 0.0284(4) Uani 1 1 d . . . . .
H9 H 0.4940 0.7149 0.4952 0.034 Uiso 1 1 calc R U . . .
C13 C 0.07422(15) 0.4143(2) 0.34459(17) 0.0214(4) Uani 1 1 d . . . . .
C12 C 0.26702(16) 0.5580(2) 0.59317(19) 0.0264(4) Uani 1 1 d . . . . .
H12 H 0.2091 0.5191 0.6189 0.032 Uiso 1 1 calc R U . . .
C10 C 0.46728(17) 0.6489(2) 0.6526(2) 0.0299(4) Uani 1 1 d . . . . .
H10 H 0.5458 0.6708 0.7177 0.036 Uiso 1 1 calc R U . . .
C11 C 0.38218(17) 0.5902(2) 0.68802(19) 0.0300(5) Uani 1 1 d . . . . .
H11 H 0.4027 0.5717 0.7782 0.036 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N2 C13 1.350(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N1 C13 1.292(2) . ?
N1 C7 1.418(2) . ?
F1A C2A 1.268(2) . ?
C1A C6A 1.389(2) . ?
C1A C2A 1.392(2) . ?
C1A C13 1.493(2) . ?
C2A C3A 1.372(3) . ?
C3A C4A 1.381(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.386(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.384(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
F1B C2B 1.262(3) . ?
C1B C2B 1.389(2) . ?
C1B C6B 1.392(2) . ?
C1B C13 1.493(2) . ?
C2B C3B 1.384(3) . ?
C3B C4B 1.386(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.381(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.372(3) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7 C12 1.392(3) . ?
C7 C8 1.397(2) . ?
C8 C9 1.377(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C12 C11 1.391(3) . ?
C12 H12 0.9500 . ?
C10 C11 1.383(3) . ?
C10 H10 0.9500 . ?
C11 H11 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
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C13 N1 C7 119.38(15) . . ?
C6A C1A C2A 116.80(17) . . ?
C6A C1A C13 121.49(14) . . ?
C2A C1A C13 121.71(15) . . ?
F1A C2A C3A 118.45(16) . . ?
F1A C2A C1A 119.33(18) . . ?
C3A C2A C1A 122.22(16) . . ?
C2A C3A C4A 119.61(16) . . ?
C2A C3A H3A 120.2 . . ?
C4A C3A H3A 120.2 . . ?
C3A C4A C5A 120.18(18) . . ?
C3A C4A H4A 119.9 . . ?
C5A C4A H4A 119.9 . . ?
C6A C5A C4A 118.97(17) . . ?
C6A C5A H5A 120.5 . . ?
C4A C5A H5A 120.5 . . ?
C5A C6A C1A 122.21(16) . . ?
C5A C6A H6A 118.9 . . ?
C1A C6A H6A 118.9 . . ?
C2B C1B C6B 116.80(17) . . ?
C2B C1B C13 121.49(14) . . ?
C6B C1B C13 121.71(15) . . ?
F1B C2B C3B 119.33(19) . . ?
F1B C2B C1B 118.19(19) . . ?
C3B C2B C1B 122.21(16) . . ?
C2B C3B C4B 118.97(17) . . ?
C2B C3B H3B 120.5 . . ?
C4B C3B H3B 120.5 . . ?
C5B C4B C3B 120.18(18) . . ?
C5B C4B H4B 119.9 . . ?
C3B C4B H4B 119.9 . . ?
C6B C5B C4B 119.61(16) . . ?
C6B C5B H5B 120.2 . . ?
C4B C5B H5B 120.2 . . ?
C5B C6B C1B 122.22(16) . . ?
C5B C6B H6B 118.9 . . ?
C1B C6B H6B 118.9 . . ?
C12 C7 C8 118.67(17) . . ?
C12 C7 N1 123.09(14) . . ?
C8 C7 N1 118.16(16) . . ?
C9 C8 C7 120.59(17) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 120.84(16) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
N1 C13 N2 121.11(17) . . ?
N1 C13 C1B 124.79(16) . . ?
N2 C13 C1B 114.09(15) . . ?
N1 C13 C1A 124.79(16) . . ?
N2 C13 C1A 114.09(15) . . ?
C11 C12 C7 120.12(15) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C11 C10 C9 118.93(18) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 120.81(18) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?

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
C6A C1A C2A F1A -179.37(18) . . . . ?
C13 C1A C2A F1A 1.1(3) . . . . ?
C6A C1A C2A C3A 0.1(3) . . . . ?
C13 C1A C2A C3A -179.49(18) . . . . ?
F1A C2A C3A C4A 179.31(19) . . . . ?
C1A C2A C3A C4A -0.1(3) . . . . ?
C2A C3A C4A C5A 0.2(3) . . . . ?
C3A C4A C5A C6A -0.1(3) . . . . ?
C4A C5A C6A C1A 0.1(3) . . . . ?
C2A C1A C6A C5A -0.1(3) . . . . ?
C13 C1A C6A C5A 179.51(18) . . . . ?
C6B C1B C2B F1B 174.0(2) . . . . ?
C13 C1B C2B F1B -6.4(3) . . . . ?
C6B C1B C2B C3B -0.1(3) . . . . ?
C13 C1B C2B C3B 179.51(18) . . . . ?
F1B C2B C3B C4B -173.9(2) . . . . ?
C1B C2B C3B C4B 0.1(3) . . . . ?
C2B C3B C4B C5B -0.1(3) . . . . ?
C3B C4B C5B C6B 0.2(3) . . . . ?
C4B C5B C6B C1B -0.1(3) . . . . ?
C2B C1B C6B C5B 0.1(3) . . . . ?
C13 C1B C6B C5B -179.49(18) . . . . ?
C13 N1 C7 C12 -59.2(2) . . . . ?
C13 N1 C7 C8 124.02(18) . . . . ?
C12 C7 C8 C9 2.5(3) . . . . ?
N1 C7 C8 C9 179.41(16) . . . . ?
C7 C8 C9 C10 -1.7(3) . . . . ?
C7 N1 C13 N2 175.38(14) . . . . ?
C7 N1 C13 C1B -5.9(2) . . . . ?
C7 N1 C13 C1A -5.9(2) . . . . ?
C2B C1B C13 N1 116.4(2) . . . . ?
C6B C1B C13 N1 -64.0(2) . . . . ?
C2B C1B C13 N2 -64.8(2) . . . . ?
C6B C1B C13 N2 114.77(19) . . . . ?
C6A C1A C13 N1 116.4(2) . . . . ?
C2A C1A C13 N1 -64.0(2) . . . . ?
C6A C1A C13 N2 -64.8(2) . . . . ?
C2A C1A C13 N2 114.77(19) . . . . ?
C8 C7 C12 C11 -2.1(3) . . . . ?
N1 C7 C12 C11 -178.82(16) . . . . ?
C8 C9 C10 C11 0.5(3) . . . . ?
C9 C10 C11 C12 0.0(3) . . . . ?
C7 C12 C11 C10 0.9(3) . . . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_DB11
_database_code_depnum_ccdc_archive 'CCDC 982078'
_audit_update_record             
;
2016-10-11 deposited with the CCDC.
2016-11-16 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            'C13 H10 F2 N2'
_chemical_formula_weight         232.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+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                   22.9004(12)
_cell_length_b                   11.9080(6)
_cell_length_c                   8.2228(5)
_cell_angle_alpha                90
_cell_angle_beta                 104.178(3)
_cell_angle_gamma                90
_cell_volume                     2174.0(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4838
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      30.11

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   0.7021
_exptl_transmission_factor_max   0.7460
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.979
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11982
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.834
_diffrn_reflns_theta_max         30.163
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3220
_reflns_number_gt                2579
_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)+(0.0840P)²+7.3794P] 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         3220
_refine_ls_number_parameters     96
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0850
_refine_ls_wR_factor_ref         0.2268
_refine_ls_wR_factor_gt          0.2131
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_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
F1A F 0.94807(12) 0.2762(2) 0.6632(3) 0.0352(5) Uani 0.538(3) 1 d D . P A 1
C1A C 0.88221(16) 0.1266(4) 0.6647(4) 0.0243(6) Uani 0.538(3) 1 d G . P A 1
C2A C 0.89767(13) 0.2234(4) 0.5905(5) 0.0243(6) Uani 0.538(3) 1 d G . P A 1
C3A C 0.86047(16) 0.2630(3) 0.4419(5) 0.0243(6) Uani 0.538(3) 1 d G . P A 1
H3A H 0.8710 0.3291 0.3912 0.029 Uiso 0.538(3) 1 calc R U P A 1
C4A C 0.80782(14) 0.2057(3) 0.3674(4) 0.0243(6) Uani 0.538(3) 1 d G . P A 1
H4A H 0.7824 0.2328 0.2657 0.029 Uiso 0.538(3) 1 calc R U P A 1
C5A C 0.79236(13) 0.1089(3) 0.4415(4) 0.0243(6) Uani 0.538(3) 1 d G . P A 1
H5A H 0.7564 0.0698 0.3906 0.029 Uiso 0.538(3) 1 calc R U P A 1
C6A C 0.82956(18) 0.0693(3) 0.5902(4) 0.0243(6) Uani 0.538(3) 1 d G . P A 1
H6A H 0.8190 0.0032 0.6409 0.029 Uiso 0.538(3) 1 calc R U P A 1
F1B F 0.80048(14) 0.0084(3) 0.6520(4) 0.0352(5) Uani 0.462(3) 1 d . . P A 2
C1B C 0.88069(18) 0.1312(4) 0.6645(5) 0.0213(6) Uani 0.462(3) 1 d G . P A 2
C2B C 0.8232(2) 0.0939(3) 0.5853(5) 0.0213(6) Uani 0.462(3) 1 d G . P A 2
C3B C 0.79157(14) 0.1451(4) 0.4381(5) 0.0213(6) Uani 0.462(3) 1 d G . P A 2
H3B H 0.7523 0.1197 0.3840 0.026 Uiso 0.462(3) 1 calc R U P A 2
C4B C 0.81738(15) 0.2335(3) 0.3701(4) 0.0213(6) Uani 0.462(3) 1 d G . P A 2
H4B H 0.7957 0.2685 0.2695 0.026 Uiso 0.462(3) 1 calc R U P A 2
C5B C 0.87484(17) 0.2708(3) 0.4493(5) 0.0213(6) Uani 0.462(3) 1 d G . P A 2
H5B H 0.8925 0.3312 0.4028 0.026 Uiso 0.462(3) 1 calc R U P A 2
C6B C 0.90650(14) 0.2196(5) 0.5965(6) 0.0213(6) Uani 0.462(3) 1 d G . P A 2
H6B H 0.9458 0.2450 0.6506 0.026 Uiso 0.462(3) 1 calc R U P A 2
F2A F 0.81225(7) 0.17176(13) 0.9214(2) 0.0336(4) Uani 0.838(3) 1 d D . P B 1
C7A C 0.91091(8) 0.24146(13) 0.9884(3) 0.0265(3) Uani 0.838(3) 1 d G . P B 1
C8A C 0.95069(6) 0.32967(15) 1.0424(3) 0.0265(3) Uani 0.838(3) 1 d G . P B 1
H8A H 0.9927 0.3185 1.0572 0.032 Uiso 0.838(3) 1 calc R U P B 1
C9A C 0.92893(7) 0.43418(13) 1.0747(3) 0.0265(3) Uani 0.838(3) 1 d G . P B 1
H9A H 0.9561 0.4945 1.1116 0.032 Uiso 0.838(3) 1 calc R U P B 1
C10A C 0.86739(8) 0.45047(12) 1.0530(3) 0.0265(3) Uani 0.838(3) 1 d G . P B 1
H10A H 0.8525 0.5219 1.0750 0.032 Uiso 0.838(3) 1 calc R U P B 1
C11A C 0.82762(6) 0.36226(16) 0.9990(3) 0.0265(3) Uani 0.838(3) 1 d G . P B 1
H11A H 0.7856 0.3734 0.9841 0.032 Uiso 0.838(3) 1 calc R U P B 1
C12A C 0.84937(8) 0.25776(15) 0.9667(4) 0.0265(3) Uani 0.838(3) 1 d DG . P B 1
F2B F 1.0057(3) 0.3070(7) 1.1073(4) 0.0336(4) Uani 0.162(3) 1 d D . P B 2
C7B C 0.9100(3) 0.2277(8) 0.9894(16) 0.0265(3) Uani 0.162(3) 1 d DG . P B 2
C8B C 0.8478(3) 0.2398(10) 0.9452(18) 0.0265(3) Uani 0.162(3) 1 d G . P B 2
H8B H 0.8230 0.1800 0.8912 0.032 Uiso 0.162(3) 1 calc R U P B 2
C9B C 0.8217(3) 0.3395(11) 0.9800(16) 0.0265(3) Uani 0.162(3) 1 d G . P B 2
H9B H 0.7791 0.3478 0.9498 0.032 Uiso 0.162(3) 1 calc R U P B 2
C10B C 0.8579(4) 0.4271(9) 1.0590(14) 0.0265(3) Uani 0.162(3) 1 d G . P B 2
H10B H 0.8400 0.4952 1.0828 0.032 Uiso 0.162(3) 1 calc R U P B 2
C11B C 0.9201(3) 0.4149(7) 1.1032(14) 0.0265(3) Uani 0.162(3) 1 d G . P B 2
H11B H 0.9449 0.4748 1.1572 0.032 Uiso 0.162(3) 1 calc R U P B 2
C12B C 0.9462(3) 0.3152(7) 1.0684(14) 0.0265(3) Uani 0.162(3) 1 d DG . P B 2
N2 N 0.93754(9) -0.02705(16) 0.8089(2) 0.0249(4) Uani 1 1 d . . . . .
H2A H 0.9604 -0.0620 0.8958 0.030 Uiso 1 1 calc R U . . .
H2B H 0.9264 -0.0614 0.7115 0.030 Uiso 1 1 calc R U . . .
N1 N 0.93551(8) 0.13081(15) 0.9677(2) 0.0222(4) Uani 1 1 d . . . . .
C13 C 0.91959(9) 0.07887(17) 0.8251(2) 0.0200(4) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1A C2A 1.322(4) . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C1A C13 1.498(3) . ?
C2A C3A 1.3900 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9500 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
F1B C2B 1.322(4) . ?
C1B C2B 1.3900 . ?
C1B C6B 1.3900 . ?
C1B C13 1.533(3) . ?
C2B C3B 1.3900 . ?
C3B C4B 1.3900 . ?
C3B H3B 0.9500 . ?
C4B C5B 1.3900 . ?
C4B H4B 0.9500 . ?
C5B C6B 1.3900 . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
F2A C12A 1.3249 . ?
C7A C8A 1.3900 . ?
C7A C12A 1.3900 . ?
C7A N1 1.459(2) . ?
C8A C9A 1.3900 . ?
C8A H8A 0.9500 . ?
C9A C10A 1.3900 . ?
C9A H9A 0.9500 . ?
C10A C11A 1.3900 . ?
C10A H10A 0.9500 . ?
C11A C12A 1.3900 . ?
C11A H11A 0.9500 . ?
F2B C12B 1.3252(10) . ?
C7B N1 1.324(9) . ?
C7B C8B 1.3900 . ?
C7B C12B 1.3900 . ?
C8B C9B 1.3900 . ?
C8B H8B 0.9500 . ?
C9B C10B 1.3900 . ?
C9B H9B 0.9500 . ?
C10B C11B 1.3900 . ?
C10B H10B 0.9500 . ?
C11B C12B 1.3900 . ?
C11B H11B 0.9500 . ?
N2 C13 1.343(3) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
N1 C13 1.296(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2A C1A C6A 120.0 . . ?
C2A C1A C13 123.3(3) . . ?
C6A C1A C13 116.7(3) . . ?
F1A C2A C1A 119.0(3) . . ?
F1A C2A C3A 121.0(3) . . ?
C1A C2A C3A 120.0 . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C5A C4A C3A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C5A C6A C1A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
C2B C1B C6B 120.0 . . ?
C2B C1B C13 123.9(3) . . ?
C6B C1B C13 116.1(3) . . ?
F1B C2B C1B 118.4(3) . . ?
F1B C2B C3B 121.6(3) . . ?
C1B C2B C3B 120.0 . . ?
C4B C3B C2B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C5B C4B C3B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C5B C6B C1B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
C8A C7A C12A 120.0 . . ?
C8A C7A N1 118.56(13) . . ?
C12A C7A N1 121.28(13) . . ?
C7A C8A C9A 120.0 . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C10A C9A C8A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C8A C9A H9A 120.0 . . ?
C9A C10A C11A 120.0 . . ?
C9A C10A H10A 120.0 . . ?
C11A C10A H10A 120.0 . . ?
C12A C11A C10A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
F2A C12A C11A 120.69(14) . . ?
F2A C12A C7A 119.26(15) . . ?
C11A C12A C7A 120.0 . . ?
N1 C7B C8B 120.9(4) . . ?
N1 C7B C12B 119.0(4) . . ?
C8B C7B C12B 120.0 . . ?
C9B C8B C7B 120.0 . . ?
C9B C8B H8B 120.0 . . ?
C7B C8B H8B 120.0 . . ?
C8B C9B C10B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B C11B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C11B C10B H10B 120.0 . . ?
C12B C11B C10B 120.0 . . ?
C12B C11B H11B 120.0 . . ?
C10B C11B H11B 120.0 . . ?
F2B C12B C11B 118.78(12) . . ?
F2B C12B C7B 121.19(11) . . ?
C11B C12B C7B 120.0 . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C13 N1 C7B 120.1(5) . . ?
C13 N1 C7A 120.36(18) . . ?
N1 C13 N2 120.84(18) . . ?
N1 C13 C1A 126.1(3) . . ?
N2 C13 C1A 113.1(2) . . ?
N1 C13 C1B 124.1(3) . . ?
N2 C13 C1B 115.0(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
C6A C1A C2A F1A -179.7(4) . . . . ?
C13 C1A C2A F1A 0.6(4) . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
C13 C1A C2A C3A -179.6(4) . . . . ?
F1A C2A C3A C4A 179.7(4) . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
C2A C1A C6A C5A 0.0 . . . . ?
C13 C1A C6A C5A 179.6(4) . . . . ?
C6B C1B C2B F1B 178.9(4) . . . . ?
C13 C1B C2B F1B 0.0(4) . . . . ?
C6B C1B C2B C3B 0.0 . . . . ?
C13 C1B C2B C3B -178.8(4) . . . . ?
F1B C2B C3B C4B -178.8(4) . . . . ?
C1B C2B C3B C4B 0.0 . . . . ?
C2B C3B C4B C5B 0.0 . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C4B C5B C6B C1B 0.0 . . . . ?
C2B C1B C6B C5B 0.0 . . . . ?
C13 C1B C6B C5B 178.9(4) . . . . ?
C12A C7A C8A C9A 0.0 . . . . ?
N1 C7A C8A C9A -175.5(2) . . . . ?
C7A C8A C9A C10A 0.0 . . . . ?
C8A C9A C10A C11A 0.0 . . . . ?
C9A C10A C11A C12A 0.0 . . . . ?
C10A C11A C12A F2A 177.4(3) . . . . ?
C10A C11A C12A C7A 0.0 . . . . ?
C8A C7A C12A F2A -177.4(3) . . . . ?
N1 C7A C12A F2A -2.0(2) . . . . ?
C8A C7A C12A C11A 0.0 . . . . ?
N1 C7A C12A C11A 175.4(2) . . . . ?
N1 C7B C8B C9B 175.4(12) . . . . ?
C12B C7B C8B C9B 0.0 . . . . ?
C7B C8B C9B C10B 0.0 . . . . ?
C8B C9B C10B C11B 0.0 . . . . ?
C9B C10B C11B C12B 0.0 . . . . ?
C10B C11B C12B F2B 178.0(10) . . . . ?
C10B C11B C12B C7B 0.0 . . . . ?
N1 C7B C12B F2B 6.6(11) . . . . ?
C8B C7B C12B F2B -177.9(11) . . . . ?
N1 C7B C12B C11B -175.5(11) . . . . ?
C8B C7B C12B C11B 0.0 . . . . ?
C8B C7B N1 C13 48.9(9) . . . . ?
C12B C7B N1 C13 -135.6(6) . . . . ?
C8A C7A N1 C13 -124.1(2) . . . . ?
C12A C7A N1 C13 60.4(2) . . . . ?
C7B N1 C13 N2 -169.2(6) . . . . ?
C7A N1 C13 N2 -173.82(19) . . . . ?
C7A N1 C13 C1A 7.7(4) . . . . ?
C7B N1 C13 C1B 11.7(6) . . . . ?
C2A C1A C13 N1 57.0(4) . . . . ?
C6A C1A C13 N1 -122.7(3) . . . . ?
C2A C1A C13 N2 -121.6(3) . . . . ?
C6A C1A C13 N2 58.7(3) . . . . ?
C2B C1B C13 N1 -114.7(3) . . . . ?
C6B C1B C13 N1 66.4(3) . . . . ?
C2B C1B C13 N2 66.1(4) . . . . ?
C6B C1B C13 N2 -112.7(3) . . . . ?

_refine_diff_density_max         1.269
_refine_diff_density_min         -0.996
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_DB23
_database_code_depnum_ccdc_archive 'CCDC 982081'
_audit_update_record             
;
2016-10-11 deposited with the CCDC.
2016-11-16 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            'C13 H10 F2 N2'
_chemical_formula_weight         232.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4875(3)
_cell_length_b                   11.5929(4)
_cell_length_c                   10.3365(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.915(2)
_cell_angle_gamma                90
_cell_volume                     1134.23(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4683
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      31.59

_exptl_crystal_description       longplate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   0.678
_exptl_transmission_factor_max   0.746
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.990
_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      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14067
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.152
_diffrn_reflns_theta_max         31.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3696
_reflns_number_gt                2804
_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)+(0.0654P)²+0.4883P] 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         3696
_refine_ls_number_parameters     158
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0574
_refine_ls_wR_factor_ref         0.1511
_refine_ls_wR_factor_gt          0.1413
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.076
_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
F1A F 0.89265(10) 0.14402(10) 0.40205(10) 0.0317(3) Uani 0.928(2) 1 d . . P A 1
C1A C 0.54973(14) 0.18213(12) 0.52810(12) 0.0165(3) Uani 0.928(2) 1 d . . P A 1
C2A C 0.55566(16) 0.09548(14) 0.62196(13) 0.0219(3) Uani 0.928(2) 1 d . . P A 1
H2A H 0.4798 0.0857 0.6763 0.026 Uiso 0.928(2) 1 calc R U P A 1
C3A C 0.67249(17) 0.02375(14) 0.63571(15) 0.0268(3) Uani 0.928(2) 1 d . . P A 1
H3A H 0.6747 -0.0360 0.6987 0.032 Uiso 0.928(2) 1 calc R U P A 1
C4A C 0.78578(16) 0.03712(14) 0.56011(15) 0.0255(3) Uani 0.928(2) 1 d . . P A 1
H4A H 0.8658 -0.0121 0.5698 0.031 Uiso 0.928(2) 1 calc R U P A 1
C5A C 0.77790(15) 0.12475(14) 0.47017(15) 0.0242(3) Uani 0.928(2) 1 d . . P A 1
C6A C 0.66228(15) 0.19608(13) 0.45000(14) 0.0210(3) Uani 0.928(2) 1 d . . P A 1
H6A H 0.6595 0.2535 0.3843 0.025 Uiso 0.928(2) 1 calc R U P A 1
F1B F 0.6777(3) -0.0591(5) 0.7236(5) 0.0317(3) Uani 0.072(2) 1 d D . P A 2
C1B C 0.54973(14) 0.18213(12) 0.52810(12) 0.0165(3) Uani 0.072(2) 1 d . . P A 2
C2B C 0.66228(15) 0.19608(13) 0.45000(14) 0.0210(3) Uani 0.072(2) 1 d . . P A 2
H2B H 0.6595 0.2535 0.3843 0.025 Uiso 0.072(2) 1 calc R U P A 2
C3B C 0.77790(15) 0.12475(14) 0.47017(15) 0.0242(3) Uani 0.072(2) 1 d . . P A 2
H3B H 0.8563 0.1367 0.4193 0.029 Uiso 0.072(2) 1 calc R U P A 2
C4B C 0.78578(16) 0.03712(14) 0.56011(15) 0.0255(3) Uani 0.072(2) 1 d . . P A 2
H4B H 0.8658 -0.0121 0.5698 0.031 Uiso 0.072(2) 1 calc DR U P A 2
C5B C 0.67249(17) 0.02375(14) 0.63571(15) 0.0268(3) Uani 0.072(2) 1 d D . P A 2
C6B C 0.55566(16) 0.09548(14) 0.62196(13) 0.0219(3) Uani 0.072(2) 1 d . . P A 2
H6B H 0.4798 0.0857 0.6763 0.026 Uiso 0.072(2) 1 calc R U P A 2
F2 F -0.06806(10) 0.59549(9) 0.32923(9) 0.0329(3) Uani 1 1 d . . . . .
N1 N 0.39242(12) 0.30231(11) 0.39612(11) 0.0183(2) Uani 1 1 d . . . . .
N2 N 0.35521(13) 0.28187(12) 0.61721(11) 0.0238(3) Uani 1 1 d . . . . .
H2C H 0.2809 0.3275 0.6122 0.029 Uiso 1 1 calc R U . . .
H2D H 0.3839 0.2502 0.6918 0.029 Uiso 1 1 calc R U . . .
C13 C 0.42528(14) 0.26044(12) 0.51037(12) 0.0163(3) Uani 1 1 d . . . . .
C7 C 0.27398(15) 0.37787(13) 0.38371(12) 0.0178(3) Uani 1 1 d . . . . .
C12 C 0.13949(15) 0.33330(14) 0.35566(13) 0.0218(3) Uani 1 1 d . . . . .
H12 H 0.1267 0.2522 0.3488 0.026 Uiso 1 1 calc DR U . . .
C10 C 0.04546(16) 0.52318(14) 0.34755(14) 0.0239(3) Uani 1 1 d . . . . .
C8 C 0.29239(16) 0.49706(14) 0.39324(14) 0.0244(3) Uani 1 1 d . . . . .
H8 H 0.3841 0.5281 0.4122 0.029 Uiso 1 1 calc R U . . .
C11 C 0.02281(16) 0.40659(15) 0.33735(14) 0.0248(3) Uani 1 1 d . . . . .
H11 H -0.0694 0.3765 0.3184 0.030 Uiso 1 1 calc R U . . .
C9 C 0.17714(18) 0.57036(15) 0.37509(15) 0.0282(3) Uani 1 1 d . . . . .
H9 H 0.1889 0.6516 0.3816 0.034 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1A C5A 1.3548(17) . ?
C1A C6A 1.3913(19) . ?
C1A C2A 1.395(2) . ?
C1A C13 1.4908(19) . ?
C2A C3A 1.385(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.380(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.376(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.378(2) . ?
C6A H6A 0.9500 . ?
F1B C5B 1.3212(10) . ?
C1B C2B 1.3913(19) . ?
C1B C6B 1.395(2) . ?
C1B C13 1.4908(19) . ?
C2B C3B 1.378(2) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.376(2) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.380(2) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.385(2) . ?
C6B H6B 0.9500 . ?
F2 C10 1.3678(17) . ?
N1 C13 1.2951(17) . ?
N1 C7 1.4237(18) . ?
N2 C13 1.3503(17) . ?
N2 H2C 0.8800 . ?
N2 H2D 0.8800 . ?
C7 C12 1.389(2) . ?
C7 C8 1.395(2) . ?
C12 C11 1.398(2) . ?
C12 H12 0.9500 . ?
C10 C11 1.372(2) . ?
C10 C9 1.376(2) . ?
C8 C9 1.387(2) . ?
C8 H8 0.9500 . ?
C11 H11 0.9500 . ?
C9 H9 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
C6A C1A C2A 119.42(13) . . ?
C6A C1A C13 119.38(12) . . ?
C2A C1A C13 121.20(12) . . ?
C3A C2A C1A 119.84(13) . . ?
C3A C2A H2A 120.1 . . ?
C1A C2A H2A 120.1 . . ?
C4A C3A C2A 121.55(14) . . ?
C4A C3A H3A 119.2 . . ?
C2A C3A H3A 119.2 . . ?
C5A C4A C3A 117.20(14) . . ?
C5A C4A H4A 121.4 . . ?
C3A C4A H4A 121.4 . . ?
F1A C5A C4A 117.68(14) . . ?
F1A C5A C6A 118.82(14) . . ?
C4A C5A C6A 123.46(14) . . ?
C5A C6A C1A 118.48(14) . . ?
C5A C6A H6A 120.8 . . ?
C1A C6A H6A 120.8 . . ?
C2B C1B C6B 119.42(13) . . ?
C2B C1B C13 119.38(12) . . ?
C6B C1B C13 121.20(12) . . ?
C3B C2B C1B 118.48(14) . . ?
C3B C2B H2B 120.8 . . ?
C1B C2B H2B 120.8 . . ?
C4B C3B C2B 123.46(14) . . ?
C4B C3B H3B 118.3 . . ?
C2B C3B H3B 118.3 . . ?
C3B C4B C5B 117.20(14) . . ?
C3B C4B H4B 121.4 . . ?
C5B C4B H4B 121.4 . . ?
F1B C5B C4B 118.50(14) . . ?
F1B C5B C6B 119.95(17) . . ?
C4B C5B C6B 121.55(14) . . ?
C5B C6B C1B 119.84(13) . . ?
C5B C6B H6B 120.1 . . ?
C1B C6B H6B 120.1 . . ?
C13 N1 C7 116.88(11) . . ?
C13 N2 H2C 120.0 . . ?
C13 N2 H2D 120.0 . . ?
H2C N2 H2D 120.0 . . ?
N1 C13 N2 125.14(13) . . ?
N1 C13 C1B 118.66(12) . . ?
N2 C13 C1B 116.20(11) . . ?
N1 C13 C1A 118.66(12) . . ?
N2 C13 C1A 116.20(11) . . ?
C12 C7 C8 119.47(13) . . ?
C12 C7 N1 119.88(13) . . ?
C8 C7 N1 120.58(13) . . ?
C7 C12 C11 120.65(14) . . ?
C7 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
F2 C10 C11 118.39(14) . . ?
F2 C10 C9 118.72(14) . . ?
C11 C10 C9 122.89(14) . . ?
C9 C8 C7 120.21(14) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C11 C12 118.04(14) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 H11 121.0 . . ?
C10 C9 C8 118.73(15) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?

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
C6A C1A C2A C3A -0.6(2) . . . . ?
C13 C1A C2A C3A 179.72(13) . . . . ?
C1A C2A C3A C4A 1.3(2) . . . . ?
C2A C3A C4A C5A -0.1(2) . . . . ?
C3A C4A C5A F1A 175.29(14) . . . . ?
C3A C4A C5A C6A -2.0(2) . . . . ?
F1A C5A C6A C1A -174.54(13) . . . . ?
C4A C5A C6A C1A 2.7(2) . . . . ?
C2A C1A C6A C5A -1.4(2) . . . . ?
C13 C1A C6A C5A 178.34(13) . . . . ?
C6B C1B C2B C3B -1.4(2) . . . . ?
C13 C1B C2B C3B 178.34(13) . . . . ?
C1B C2B C3B C4B 2.7(2) . . . . ?
C2B C3B C4B C5B -2.0(2) . . . . ?
C3B C4B C5B F1B -179.4(4) . . . . ?
C3B C4B C5B C6B -0.1(2) . . . . ?
F1B C5B C6B C1B -179.3(4) . . . . ?
C4B C5B C6B C1B 1.3(2) . . . . ?
C2B C1B C6B C5B -0.6(2) . . . . ?
C13 C1B C6B C5B 179.72(13) . . . . ?
C7 N1 C13 N2 0.8(2) . . . . ?
C7 N1 C13 C1B -179.22(12) . . . . ?
C7 N1 C13 C1A -179.22(12) . . . . ?
C2B C1B C13 N1 30.09(19) . . . . ?
C6B C1B C13 N1 -150.21(14) . . . . ?
C2B C1B C13 N2 -149.94(14) . . . . ?
C6B C1B C13 N2 29.76(19) . . . . ?
C6A C1A C13 N1 30.09(19) . . . . ?
C2A C1A C13 N1 -150.21(14) . . . . ?
C6A C1A C13 N2 -149.94(14) . . . . ?
C2A C1A C13 N2 29.76(19) . . . . ?
C13 N1 C7 C12 -88.98(16) . . . . ?
C13 N1 C7 C8 94.15(16) . . . . ?
C8 C7 C12 C11 -0.2(2) . . . . ?
N1 C7 C12 C11 -177.10(12) . . . . ?
C12 C7 C8 C9 0.1(2) . . . . ?
N1 C7 C8 C9 177.02(13) . . . . ?
F2 C10 C11 C12 179.73(12) . . . . ?
C9 C10 C11 C12 -0.1(2) . . . . ?
C7 C12 C11 C10 0.2(2) . . . . ?
F2 C10 C9 C8 -179.78(13) . . . . ?
C11 C10 C9 C8 0.1(2) . . . . ?
C7 C8 C9 C10 -0.1(2) . . . . ?

_refine_diff_density_max         0.856
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_DB33
_database_code_depnum_ccdc_archive 'CCDC 982085'
_audit_update_record             
;
2016-06-27 deposited with the CCDC.
2016-11-16 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            'C13 H10 F2 N2'
_chemical_formula_weight         232.23

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6935(3)
_cell_length_b                   10.9094(3)
_cell_length_c                   10.3672(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.576(2)
_cell_angle_gamma                90
_cell_volume                     1092.84(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5019
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      30.17

_exptl_crystal_description       longplate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.109
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8976
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.108
_diffrn_reflns_theta_max         27.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2452
_reflns_number_gt                2162
_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)+(0.0469P)²+0.4539P] 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         2452
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0380
_refine_ls_wR_factor_ref         0.1003
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
F2 F -0.06018(8) -0.12113(7) 0.85276(7) 0.0252(2) Uani 1 1 d . . . . .
F1 F 0.87762(8) 0.56322(7) 1.04810(8) 0.0259(2) Uani 1 1 d . . . . .
N1 N 0.39238(10) 0.19108(9) 0.89267(9) 0.0158(2) Uani 1 1 d . . . . .
N2 N 0.35903(11) 0.21866(10) 1.11176(10) 0.0193(2) Uani 1 1 d . . . . .
H2A H 0.2871 0.1692 1.1079 0.023 Uiso 1 1 calc R U . . .
H2B H 0.3870 0.2544 1.1853 0.023 Uiso 1 1 calc R U . . .
C1 C 0.54784(11) 0.32460(10) 1.01861(11) 0.0142(2) Uani 1 1 d . . . . .
C2 C 0.57501(12) 0.39611(11) 1.12904(11) 0.0165(3) Uani 1 1 d . . . . .
H2 H 0.5164 0.3900 1.1979 0.020 Uiso 1 1 calc R U . . .
C3 C 0.68679(12) 0.47619(11) 1.13972(12) 0.0191(3) Uani 1 1 d . . . . .
H3 H 0.7054 0.5244 1.2154 0.023 Uiso 1 1 calc R U . . .
C4 C 0.76984(12) 0.48416(11) 1.03858(12) 0.0183(3) Uani 1 1 d . . . . .
C5 C 0.74657(13) 0.41532(12) 0.92741(12) 0.0198(3) Uani 1 1 d . . . . .
H5 H 0.8056 0.4225 0.8589 0.024 Uiso 1 1 calc R U . . .
C6 C 0.63498(12) 0.33535(11) 0.91788(12) 0.0181(3) Uani 1 1 d . . . . .
H6 H 0.6175 0.2872 0.8420 0.022 Uiso 1 1 calc R U . . .
C7 C 0.27674(12) 0.10979(11) 0.88473(11) 0.0154(2) Uani 1 1 d . . . . .
C8 C 0.14758(12) 0.15267(11) 0.83608(12) 0.0182(3) Uani 1 1 d . . . . .
H8 H 0.1373 0.2361 0.8108 0.022 Uiso 1 1 calc R U . . .
C9 C 0.03377(12) 0.07515(12) 0.82406(12) 0.0198(3) Uani 1 1 d . . . . .
H9 H -0.0543 0.1043 0.7906 0.024 Uiso 1 1 calc R U . . .
C10 C 0.05187(12) -0.04490(12) 0.86188(11) 0.0181(3) Uani 1 1 d . . . . .
C11 C 0.17763(13) -0.09159(12) 0.90920(12) 0.0206(3) Uani 1 1 d . . . . .
H11 H 0.1868 -0.1753 0.9337 0.025 Uiso 1 1 calc R U . . .
C12 C 0.29108(13) -0.01321(12) 0.92031(12) 0.0189(3) Uani 1 1 d . . . . .
H12 H 0.3790 -0.0436 0.9524 0.023 Uiso 1 1 calc R U . . .
C13 C 0.42656(12) 0.23978(11) 1.00456(11) 0.0142(2) 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
F2 C10 1.3653(13) . ?
F1 C4 1.3523(13) . ?
N1 C13 1.2948(15) . ?
N1 C7 1.4266(14) . ?
N2 C13 1.3537(15) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?
C1 C2 1.3930(16) . ?
C1 C6 1.3994(16) . ?
C1 C13 1.4941(16) . ?
C2 C3 1.3894(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3748(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3790(18) . ?
C5 C6 1.3871(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.3929(16) . ?
C7 C12 1.3956(17) . ?
C8 C9 1.3877(17) . ?
C8 H8 0.9500 . ?
C9 C10 1.3743(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.3750(17) . ?
C11 C12 1.3905(17) . ?
C11 H11 0.9500 . ?
C12 H12 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
C13 N1 C7 116.78(10) . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
C2 C1 C6 118.72(11) . . ?
C2 C1 C13 121.51(10) . . ?
C6 C1 C13 119.75(10) . . ?
C3 C2 C1 120.85(11) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C4 C3 C2 118.65(11) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
F1 C4 C3 118.73(11) . . ?
F1 C4 C5 118.84(11) . . ?
C3 C4 C5 122.43(11) . . ?
C4 C5 C6 118.47(11) . . ?
C4 C5 H5 120.8 . . ?
C6 C5 H5 120.8 . . ?
C5 C6 C1 120.88(11) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C8 C7 C12 119.10(11) . . ?
C8 C7 N1 119.45(11) . . ?
C12 C7 N1 121.42(11) . . ?
C9 C8 C7 120.87(11) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 118.20(11) . . ?
C10 C9 H9 120.9 . . ?
C8 C9 H9 120.9 . . ?
F2 C10 C9 118.55(11) . . ?
F2 C10 C11 118.48(11) . . ?
C9 C10 C11 122.97(11) . . ?
C10 C11 C12 118.33(12) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C11 C12 C7 120.53(11) . . ?
C11 C12 H12 119.7 . . ?
C7 C12 H12 119.7 . . ?
N1 C13 N2 124.04(11) . . ?
N1 C13 C1 118.98(10) . . ?
N2 C13 C1 116.98(10) . . ?

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
C6 C1 C2 C3 -0.36(17) . . . . ?
C13 C1 C2 C3 -178.84(11) . . . . ?
C1 C2 C3 C4 0.43(18) . . . . ?
C2 C3 C4 F1 179.15(11) . . . . ?
C2 C3 C4 C5 -0.28(19) . . . . ?
F1 C4 C5 C6 -179.36(11) . . . . ?
C3 C4 C5 C6 0.07(19) . . . . ?
C4 C5 C6 C1 0.00(18) . . . . ?
C2 C1 C6 C5 0.14(17) . . . . ?
C13 C1 C6 C5 178.65(11) . . . . ?
C13 N1 C7 C8 99.14(13) . . . . ?
C13 N1 C7 C12 -83.21(14) . . . . ?
C12 C7 C8 C9 0.66(18) . . . . ?
N1 C7 C8 C9 178.37(11) . . . . ?
C7 C8 C9 C10 0.23(18) . . . . ?
C8 C9 C10 F2 178.72(10) . . . . ?
C8 C9 C10 C11 -0.90(18) . . . . ?
F2 C10 C11 C12 -178.98(10) . . . . ?
C9 C10 C11 C12 0.63(18) . . . . ?
C10 C11 C12 C7 0.31(18) . . . . ?
C8 C7 C12 C11 -0.93(18) . . . . ?
N1 C7 C12 C11 -178.60(11) . . . . ?
C7 N1 C13 N2 -0.50(17) . . . . ?
C7 N1 C13 C1 179.36(10) . . . . ?
C2 C1 C13 N1 168.56(11) . . . . ?
C6 C1 C13 N1 -9.91(16) . . . . ?
C2 C1 C13 N2 -11.57(16) . . . . ?
C6 C1 C13 N2 169.96(11) . . . . ?

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.051

