# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_db12
_database_code_depnum_ccdc_archive 'CCDC 982079'
_audit_update_record             
;
2014-01-17 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_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                   23.4570(13)
_cell_length_b                   11.7906(6)
_cell_length_c                   8.1237(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.585(4)
_cell_angle_gamma                90.00
_cell_volume                     2192.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      28.76

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9578
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9243
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_av_sigmaI/netI    0.0642
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         1.78
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2515
_reflns_number_gt                1445
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0741P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2515
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0555
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1305
_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
_iucr_refine_instruction_details 
;
TITL    DB12 in C2/c
CELL 0.71073 23.4570 11.7906 8.1237 90.000 102.585 90.000
ZERR 8.00 0.0013 0.0006 0.0005 0.000 0.004 0.000
LATT  7
SYMM -X,Y, 0.50000-Z
SFAC    C   H   N   F
UNIT   104  80  16  16
MERG    2
L.S.    12
ACTA
BOND $H
HTAB
CONF
SIZE 0.4 0.15 0.1
TEMP -173
EADP F1A F1B
EADP F2A F2B
EXYZ C1A C1B
EXYZ C2A C6B
EXYZ C3A C5B
EXYZ C4A C4B
EXYZ C5A C3B
EXYZ C6A C2B
 
EADP C1A C1B
EADP C2A C6B
EADP C3A C5B
EADP C4A C4B
EADP C5A C3B
EADP C6A C2B
 
EXYZ C7A C7B
EXYZ C8A C12B
EXYZ C9A C11B
EXYZ C10A C10B
EXYZ C11A C9B
EXYZ C12A C8B
 
EADP C7A C7B
EADP C8A C12B
EADP C9A C11B
EADP C10A C10B
EADP C11A C9B
EADP C12A C8B
FMAP    2
PLAN    10
 
WGHT    0.074100
FVAR       0.12201   0.82475   0.90140
PART 1
F1A   4    0.444382    0.276994    0.657844    21.00000    0.04315    0.04085 =
         0.03594    0.00799    0.00494   -0.01270
C1A   1    0.382726    0.123262    0.669037    21.00000    0.03078    0.02606 =
         0.02203    0.00080    0.00692    0.00415
C2A   1    0.396786    0.219707    0.590309    21.00000    0.04156    0.02552 =
         0.02818   -0.00203    0.00421   -0.00349
C3A   1    0.361920    0.262959    0.445201    21.00000    0.06641    0.02644 =
         0.02948    0.00282    0.01204    0.00724
AFIX  43
H3A   2    0.373034    0.329338    0.393775    21.00000   -1.20000
AFIX   0
C4A   1    0.310557    0.207549    0.376587    21.00000    0.04489    0.05204 =
         0.02837   -0.00116    0.00186    0.01928
AFIX  43
H4A   2    0.285509    0.236539    0.277626    21.00000   -1.20000
AFIX   0
C5A   1    0.295333    0.110644    0.450369    21.00000    0.03539    0.06451 =
         0.03363   -0.00117    0.00293    0.00013
AFIX  43
H5A   2    0.259919    0.072590    0.402307    21.00000   -1.20000
AFIX   0
C6A   1    0.331468    0.068749    0.594058    21.00000    0.03351    0.05147 =
         0.02640    0.00175    0.00627   -0.00320
AFIX  43
H6A   2    0.320941    0.000800    0.642840    21.00000   -1.20000
AFIX   0
PART 2
F1B   4    0.308878    0.003567    0.661688   -21.00000    0.04315    0.04085 =
         0.03594    0.00799    0.00494   -0.01270
C1B   1    0.382726    0.123262    0.669037   -21.00000    0.03078    0.02606 =
         0.02203    0.00080    0.00692    0.00415
C2B   1    0.331468    0.068749    0.594058   -21.00000    0.03351    0.05147 =
         0.02640    0.00175    0.00627   -0.00320
C3B   1    0.295333    0.110644    0.450369   -21.00000    0.03539    0.06451 =
         0.03363   -0.00117    0.00293    0.00013
AFIX  43
H3B   2    0.259919    0.072590    0.402307   -21.00000   -1.20000
AFIX   0
C4B   1    0.310557    0.207549    0.376587   -21.00000    0.04489    0.05204 =
         0.02837   -0.00116    0.00186    0.01928
AFIX  43
H4B   2    0.285509    0.236539    0.277626   -21.00000   -1.20000
AFIX   0
C5B   1    0.361920    0.262959    0.445201   -21.00000    0.06641    0.02644 =
         0.02948    0.00282    0.01204    0.00724
AFIX  43
H5B   2    0.373034    0.329338    0.393775   -21.00000   -1.20000
AFIX   0
C6B   1    0.396786    0.219707    0.590309   -21.00000    0.04156    0.02552 =
         0.02818   -0.00203    0.00421   -0.00349
AFIX  43
H6B   2    0.432117    0.258050    0.638326   -21.00000   -1.20000
AFIX   0
 
PART 0
PART 1
F2A   4    0.275663    0.371363    0.992446    31.00000    0.03643    0.04154 =
         0.05876   -0.00241    0.00819    0.01070
C7A   1    0.414086    0.238539    0.989971    31.00000    0.03771    0.02342 =
         0.02268    0.00497    0.00765    0.00450
C8A   1    0.450998    0.328164    1.050940    31.00000    0.03886    0.02818 =
         0.04096   -0.00180    0.01075   -0.00176
AFIX  43
H8A   2    0.492085    0.318824    1.067561    31.00000   -1.20000
AFIX   0
C9A   1    0.428279    0.431116    1.087680    31.00000    0.05186    0.02330 =
         0.05661   -0.00566    0.01899   -0.00293
AFIX  43
H9A   2    0.454152    0.492017    1.127330    31.00000   -1.20000
AFIX   0
C10A  1    0.369200    0.447260    1.068140    31.00000    0.05696    0.02255 =
         0.04341    0.00013    0.01715    0.00528
AFIX  43
H10A  2    0.353715    0.517610    1.095081    31.00000   -1.20000
AFIX   0
C11A  1    0.333650    0.357874    1.008325    31.00000    0.03675    0.03517 =
         0.03529    0.00557    0.01075    0.01101
C12A  1    0.354050    0.253412    0.969558    31.00000    0.03767    0.02872 =
         0.02747    0.00085    0.00694    0.00353
AFIX  43
H12A  2    0.327734    0.193177    0.929919    31.00000   -1.20000
AFIX   0
PART 2
F2B   4    0.452589    0.515303    1.120221   -31.00000    0.03643    0.04154 =
         0.05876   -0.00241    0.00819    0.01070
C7B   1    0.414086    0.238539    0.989971   -31.00000    0.03771    0.02342 =
         0.02268    0.00497    0.00765    0.00450
C8B   1    0.354050    0.253412    0.969558   -31.00000    0.03767    0.02872 =
         0.02747    0.00085    0.00694    0.00353
AFIX  43
H8B   2    0.327734    0.193177    0.929919   -31.00000   -1.20000
AFIX   0
C9B   1    0.333650    0.357874    1.008325   -31.00000    0.03675    0.03517 =
         0.03529    0.00557    0.01075    0.01101
AFIX  43
H9B   2    0.292639    0.368057    0.992491   -31.00000   -1.20000
AFIX   0
C10B  1    0.369200    0.447260    1.068140   -31.00000    0.05696    0.02255 =
         0.04341    0.00013    0.01715    0.00528
AFIX  43
H10B  2    0.353715    0.517610    1.095081   -31.00000   -1.20000
AFIX   0
C11B  1    0.428279    0.431116    1.087680   -31.00000    0.05186    0.02330 =
         0.05661   -0.00566    0.01899   -0.00293
C12B  1    0.450998    0.328164    1.050940   -31.00000    0.03886    0.02818 =
         0.04096   -0.00180    0.01075   -0.00176
AFIX  43
H12B  2    0.492085    0.318824    1.067561   -31.00000   -1.20000
AFIX   0
 
PART 0
N1    3    0.438853    0.131981    0.965680    11.00000    0.03412    0.02183 =
         0.02699    0.00122    0.00648    0.00313
N2    3    0.439868   -0.029630    0.809881    11.00000    0.03914    0.02167 =
         0.02537    0.00003    0.00399    0.00311
AFIX  93
H2A   2    0.463184   -0.063034    0.895730    11.00000   -1.20000
H2B   2    0.428267   -0.066303    0.714081    11.00000   -1.20000
AFIX   0
 
C13   1    0.421999    0.077253    0.825059    11.00000    0.02843    0.02352 =
         0.02463    0.00213    0.00852   -0.00173
HKLF   4
 

END  

;


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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 0.44438(7) 0.27699(13) 0.65784(19) 0.0405(5) Uani 0.825(2) 1 d P A 1
C1A C 0.38273(9) 0.12326(17) 0.6690(3) 0.0261(5) Uani 0.825(2) 1 d P A 1
C2A C 0.39679(10) 0.21971(18) 0.5903(3) 0.0323(6) Uani 0.825(2) 1 d P A 1
C3A C 0.36192(12) 0.26296(19) 0.4452(3) 0.0405(6) Uani 0.825(2) 1 d P A 1
H3A H 0.3730 0.3293 0.3938 0.049 Uiso 0.825(2) 1 calc PR A 1
C4A C 0.31056(11) 0.2075(2) 0.3766(3) 0.0427(7) Uani 0.825(2) 1 d P A 1
H4A H 0.2855 0.2365 0.2776 0.051 Uiso 0.825(2) 1 calc PR A 1
C5A C 0.29533(11) 0.1106(2) 0.4504(3) 0.0452(7) Uani 0.825(2) 1 d P A 1
H5A H 0.2599 0.0726 0.4023 0.054 Uiso 0.825(2) 1 calc PR A 1
C6A C 0.33147(10) 0.0687(2) 0.5941(3) 0.0372(6) Uani 0.825(2) 1 d P A 1
H6A H 0.3209 0.0008 0.6428 0.045 Uiso 0.825(2) 1 calc PR A 1
F1B F 0.3089(3) 0.0036(6) 0.6617(9) 0.0405(5) Uani 0.175(2) 1 d P A 2
C1B C 0.38273(9) 0.12326(17) 0.6690(3) 0.0261(5) Uani 0.175(2) 1 d P A 2
C2B C 0.33147(10) 0.0687(2) 0.5941(3) 0.0372(6) Uani 0.175(2) 1 d P A 2
C3B C 0.29533(11) 0.1106(2) 0.4504(3) 0.0452(7) Uani 0.175(2) 1 d P A 2
H3B H 0.2599 0.0726 0.4023 0.054 Uiso 0.175(2) 1 calc PR A 2
C4B C 0.31056(11) 0.2075(2) 0.3766(3) 0.0427(7) Uani 0.175(2) 1 d P A 2
H4B H 0.2855 0.2365 0.2776 0.051 Uiso 0.175(2) 1 calc PR A 2
C5B C 0.36192(12) 0.26296(19) 0.4452(3) 0.0405(6) Uani 0.175(2) 1 d P A 2
H5B H 0.3730 0.3293 0.3938 0.049 Uiso 0.175(2) 1 calc PR A 2
C6B C 0.39679(10) 0.21971(18) 0.5903(3) 0.0323(6) Uani 0.175(2) 1 d P A 2
H6B H 0.4321 0.2581 0.6383 0.039 Uiso 0.175(2) 1 calc PR A 2
F2A F 0.27566(6) 0.37136(12) 0.9924(2) 0.0459(5) Uani 0.901(2) 1 d P B 1
C7A C 0.41409(10) 0.23854(17) 0.9900(3) 0.0278(5) Uani 0.901(2) 1 d P B 1
C8A C 0.45100(10) 0.32816(18) 1.0509(3) 0.0357(6) Uani 0.901(2) 1 d P B 1
H8A H 0.4921 0.3188 1.0676 0.043 Uiso 0.901(2) 1 calc PR B 1
C9A C 0.42828(11) 0.43112(19) 1.0877(3) 0.0428(6) Uani 0.901(2) 1 d P B 1
H9A H 0.4542 0.4920 1.1273 0.051 Uiso 0.901(2) 1 calc PR B 1
C10A C 0.36920(11) 0.44726(19) 1.0681(3) 0.0400(6) Uani 0.901(2) 1 d P B 1
H10A H 0.3537 0.5176 1.0951 0.048 Uiso 0.901(2) 1 calc PR B 1
C11A C 0.33365(10) 0.35787(19) 1.0083(3) 0.0353(6) Uani 0.901(2) 1 d P B 1
C12A C 0.35405(10) 0.25341(18) 0.9696(3) 0.0313(6) Uani 0.901(2) 1 d P B 1
H12A H 0.3277 0.1932 0.9299 0.038 Uiso 0.901(2) 1 calc PR B 1
F2B F 0.4526(5) 0.5153(12) 1.1202(18) 0.0459(5) Uani 0.099(2) 1 d P B 2
C7B C 0.41409(10) 0.23854(17) 0.9900(3) 0.0278(5) Uani 0.099(2) 1 d P B 2
C8B C 0.35405(10) 0.25341(18) 0.9696(3) 0.0313(6) Uani 0.099(2) 1 d P B 2
H8B H 0.3277 0.1932 0.9299 0.038 Uiso 0.099(2) 1 calc PR B 2
C9B C 0.33365(10) 0.35787(19) 1.0083(3) 0.0353(6) Uani 0.099(2) 1 d P B 2
H9B H 0.2926 0.3681 0.9925 0.042 Uiso 0.099(2) 1 calc PR B 2
C10B C 0.36920(11) 0.44726(19) 1.0681(3) 0.0400(6) Uani 0.099(2) 1 d P B 2
H10B H 0.3537 0.5176 1.0951 0.048 Uiso 0.099(2) 1 calc PR B 2
C11B C 0.42828(11) 0.43112(19) 1.0877(3) 0.0428(6) Uani 0.099(2) 1 d P B 2
C12B C 0.45100(10) 0.32816(18) 1.0509(3) 0.0357(6) Uani 0.099(2) 1 d P B 2
H12B H 0.4921 0.3188 1.0676 0.043 Uiso 0.099(2) 1 calc PR B 2
N1 N 0.43885(7) 0.13198(13) 0.9657(2) 0.0277(4) Uani 1 1 d . . .
N2 N 0.43987(7) -0.02963(13) 0.8099(2) 0.0292(5) Uani 1 1 d . . .
H2A H 0.4632 -0.0630 0.8957 0.035 Uiso 1 1 calc R B .
H2B H 0.4283 -0.0663 0.7141 0.035 Uiso 1 1 calc R . .
C13 C 0.42200(9) 0.07725(17) 0.8251(3) 0.0251(5) Uani 1 1 d . A .


_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 1.318(2) . ?
C1A C2A 1.379(3) . ?
C1A C6A 1.382(3) . ?
C1A C13 1.497(3) . ?
C2A C3A 1.378(3) . ?
C3A C4A 1.377(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.373(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.376(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
F2A C11A 1.347(3) . ?
C7A C8A 1.387(3) . ?
C7A C12A 1.393(3) . ?
C7A N1 1.416(2) . ?
C8A C9A 1.384(3) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.373(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.366(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.382(3) . ?
C12A H12A 0.9500 . ?
N1 C13 1.296(3) . ?
N2 C13 1.342(2) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?

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 116.9(2) . . ?
C2A C1A C13 121.74(19) . . ?
C6A C1A C13 121.36(19) . . ?
F1A C2A C3A 117.2(2) . . ?
F1A C2A C1A 119.7(2) . . ?
C3A C2A C1A 123.0(2) . . ?
C4A C3A C2A 118.3(2) . . ?
C4A C3A H3A 120.8 . . ?
C2A C3A H3A 120.8 . . ?
C5A C4A C3A 120.4(2) . . ?
C5A C4A H4A 119.8 . . ?
C3A C4A H4A 119.8 . . ?
C4A C5A C6A 119.9(2) . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A H5A 120.1 . . ?
C5A C6A C1A 121.5(2) . . ?
C5A C6A H6A 119.2 . . ?
C1A C6A H6A 119.2 . . ?
C8A C7A C12A 118.87(19) . . ?
C8A C7A N1 118.8(2) . . ?
C12A C7A N1 122.01(19) . . ?
C9A C8A C7A 120.4(2) . . ?
C9A C8A H8A 119.8 . . ?
C7A C8A H8A 119.8 . . ?
C10A C9A C8A 121.5(2) . . ?
C10A C9A H9A 119.2 . . ?
C8A C9A H9A 119.2 . . ?
C11A C10A C9A 117.2(2) . . ?
C11A C10A H10A 121.4 . . ?
C9A C10A H10A 121.4 . . ?
F2A C11A C10A 117.9(2) . . ?
F2A C11A C12A 118.4(2) . . ?
C10A C11A C12A 123.6(2) . . ?
C11A C12A C7A 118.4(2) . . ?
C11A C12A H12A 120.8 . . ?
C7A C12A H12A 120.8 . . ?
C13 N1 C7A 120.59(18) . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C13 N2 120.46(19) . . ?
N1 C13 C1A 125.38(19) . . ?
N2 C13 C1A 114.17(18) . . ?

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 178.4(2) . . . . ?
C13 C1A C2A F1A -3.7(3) . . . . ?
C6A C1A C2A C3A 1.0(3) . . . . ?
C13 C1A C2A C3A 179.0(2) . . . . ?
F1A C2A C3A C4A -177.0(2) . . . . ?
C1A C2A C3A C4A 0.4(4) . . . . ?
C2A C3A C4A C5A -1.0(4) . . . . ?
C3A C4A C5A C6A 0.2(4) . . . . ?
C4A C5A C6A C1A 1.3(4) . . . . ?
C2A C1A C6A C5A -1.9(3) . . . . ?
C13 C1A C6A C5A -179.8(2) . . . . ?
C12A C7A C8A C9A -1.2(3) . . . . ?
N1 C7A C8A C9A -175.3(2) . . . . ?
C7A C8A C9A C10A 1.2(4) . . . . ?
C8A C9A C10A C11A -1.0(4) . . . . ?
C9A C10A C11A F2A 178.4(2) . . . . ?
C9A C10A C11A C12A 0.9(4) . . . . ?
F2A C11A C12A C7A -178.42(19) . . . . ?
C10A C11A C12A C7A -1.0(3) . . . . ?
C8A C7A C12A C11A 1.1(3) . . . . ?
N1 C7A C12A C11A 175.03(19) . . . . ?
C8A C7A N1 C13 -131.0(2) . . . . ?
C12A C7A N1 C13 55.0(3) . . . . ?
C7A N1 C13 N2 -171.44(18) . . . . ?
C7A N1 C13 C1A 8.8(3) . . . . ?
C2A C1A C13 N1 58.3(3) . . . . ?
C6A C1A C13 N1 -123.8(2) . . . . ?
C2A C1A C13 N2 -121.5(2) . . . . ?
C6A C1A C13 N2 56.4(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.326
_refine_diff_density_min         -0.306
_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_DE1
_database_code_depnum_ccdc_archive 'CCDC 1016404'
_audit_update_record             
;
2014-07-28 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_Int_Tables_number      14

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

_cell_length_a                   12.7028(17)
_cell_length_b                   8.3775(8)
_cell_length_c                   11.5509(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 117.017(5)
_cell_angle_gamma                90.00
_cell_volume                     1095.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      30.07

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9660
_exptl_absorpt_correction_T_max  0.9849
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29721
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.03
_diffrn_reflns_theta_max         29.57
_reflns_number_total             3065
_reflns_number_gt                2378
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0679P)²+0.6568P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3065
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0685
_refine_ls_R_factor_gt           0.0503
_refine_ls_wR_factor_ref         0.1379
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_iucr_refine_instruction_details 
;
TITL DB12_N in P2(1)/c
CELL 0.71073 12.7028 8.3775 11.5509 90.000 117.017 90.000
ZERR 4.00 0.0017 0.0008 0.0012 0.000 0.005 0.000
LATT 1
SYMM -X, 0.50000+Y, 0.50000-Z
SFAC C   H   N   F
UNIT 52  40  8   8
MERG 2
L.S. 12
ACTA
BOND $H
CONF
HTAB
SIZE 0.31 0.32 0.14
TEMP -173
EADP F1A F1B
EADP F2A F2B
EXYZ C1A C1B
EXYZ C2A C6B
EXYZ C3A C5B
EXYZ C4A C4B
EXYZ C5A C3B
EXYZ C6A C2B
EADP C1A C1B
EADP C2A C6B
EADP C3A C5B
EADP C4A C4B
EADP C5A C3B
EADP C6A C2B
EXYZ C7A C7B
EXYZ C8A C12B
EXYZ C9A C11B
EXYZ C10A C10B
EXYZ C11A C9B
EXYZ C12A C8B
EADP C7A C7B
EADP C8A C12B
EADP C9A C11B
EADP C10A C10B
EADP C11A C9B
EADP C12A C8B
FMAP    2
PLAN    5
WGHT    0.067900    0.656800
FVAR       0.27717   0.52258   0.89323
PART 1
F1A   4    0.728125    0.225885    0.660856    21.00000    0.02994    0.02377 =
         0.03238    0.00701    0.02159    0.00615
C1A   1    0.864276    0.229709    0.579402    21.00000    0.01632    0.01160 =
         0.01361   -0.00104    0.00241   -0.00108
C2A   1    0.766706    0.293046    0.587408    21.00000    0.01675    0.01462 =
         0.02031   -0.00009    0.00530   -0.00148
C3A   1    0.707537    0.426407    0.516310    21.00000    0.01698    0.01560 =
         0.02525   -0.00211    0.00438    0.00123
AFIX  43
H3A   2    0.640964    0.467721    0.523208    21.00000   -1.20000
AFIX   0
C4A   1    0.747035    0.498610    0.434934    21.00000    0.02516    0.01289 =
         0.01921    0.00146    0.00056    0.00130
AFIX  43
H4A   2    0.707269    0.590055    0.385952    21.00000   -1.20000
AFIX   0
C5A   1    0.844071    0.438186    0.424678    21.00000    0.03166    0.01669 =
         0.01610    0.00214    0.00858   -0.00159
AFIX  43
H5A   2    0.870808    0.487423    0.368731    21.00000   -1.20000
AFIX   0
C6A   1    0.901838    0.304527    0.497337    21.00000    0.02446    0.01609 =
         0.01821   -0.00122    0.00910    0.00050
AFIX  43
H6A   2    0.968576    0.263460    0.490650    21.00000   -1.20000
AFIX   0
PART 2
F1B   4    0.986456    0.239320    0.480825   -21.00000    0.02994    0.02377 =
         0.03238    0.00701    0.02159    0.00615
C1B   1    0.864276    0.229709    0.579402   -21.00000    0.01632    0.01160 =
         0.01361   -0.00104    0.00241   -0.00108
C2B   1    0.901838    0.304527    0.497337   -21.00000    0.02446    0.01609 =
         0.01821   -0.00122    0.00910    0.00050
C3B   1    0.844071    0.438186    0.424678   -21.00000    0.03166    0.01669 =
         0.01610    0.00214    0.00858   -0.00159
AFIX  43
H3B   2    0.870808    0.487423    0.368731   -21.00000   -1.20000
AFIX   0
C4B   1    0.747035    0.498610    0.434934   -21.00000    0.02516    0.01289 =
         0.01921    0.00146    0.00056    0.00130
AFIX  43
H4B   2    0.707269    0.590055    0.385952   -21.00000   -1.20000
AFIX   0
C5B   1    0.707537    0.426407    0.516310   -21.00000    0.01698    0.01560 =
         0.02525   -0.00211    0.00438    0.00123
AFIX  43
H5B   2    0.640964    0.467721    0.523208   -21.00000   -1.20000
AFIX   0
C6B   1    0.766706    0.293046    0.587408   -21.00000    0.01675    0.01462 =
         0.02031   -0.00009    0.00530   -0.00148
AFIX  43
H6B   2    0.739730    0.243697    0.643103   -21.00000   -1.20000
AFIX   0
PART 0
PART 1
F2A   4    0.583165   -0.045731    0.195394    31.00000    0.03452    0.03482 =
         0.01532    0.00001    0.00393   -0.00366
C7A   1    0.764032   -0.082109    0.542307    31.00000    0.01719    0.00967 =
         0.01849   -0.00090    0.00181    0.00130
C8A   1    0.681137   -0.150079    0.575317    31.00000    0.02199    0.01678 =
         0.02187    0.00038    0.00603   -0.00042
AFIX  43
H8A   2    0.703248   -0.175821    0.663475    31.00000   -1.20000
AFIX   0
C9A   1    0.566684   -0.180628    0.480999    31.00000    0.01983    0.02125 =
         0.03241   -0.00044    0.00730   -0.00235
AFIX  43
H9A   2    0.511221   -0.225861    0.505592    31.00000   -1.20000
AFIX   0
C10A  1    0.532237   -0.145971    0.351303    31.00000    0.01940    0.02010 =
         0.02869   -0.00210   -0.00058    0.00022
AFIX  43
H10A  2    0.453982   -0.165967    0.286210    31.00000   -1.20000
AFIX   0
C11A  1    0.615885   -0.081656    0.321042    31.00000    0.02888    0.01780 =
         0.01574   -0.00052    0.00043    0.00244
C12A  1    0.731847   -0.050037    0.411738    31.00000    0.02406    0.01439 =
         0.01988   -0.00079    0.00650   -0.00169
AFIX  43
H12A  2    0.787333   -0.008030    0.385782    31.00000   -1.20000
AFIX   0
PART 2
F2B   4    0.489261   -0.227634    0.490270   -31.00000    0.03452    0.03482 =
         0.01532    0.00001    0.00393   -0.00366
C7B   1    0.764032   -0.082109    0.542307   -31.00000    0.01719    0.00967 =
         0.01849   -0.00090    0.00181    0.00130
C8B   1    0.731847   -0.050037    0.411738   -31.00000    0.02406    0.01439 =
         0.01988   -0.00079    0.00650   -0.00169
AFIX  43
H8B   2    0.787333   -0.008030    0.385782   -31.00000   -1.20000
AFIX   0
C9B   1    0.615885   -0.081656    0.321042   -31.00000    0.02888    0.01780 =
         0.01574   -0.00052    0.00043    0.00244
AFIX  43
H9B   2    0.593246   -0.057126    0.232559   -31.00000   -1.20000
AFIX   0
C10B  1    0.532237   -0.145971    0.351303   -31.00000    0.01940    0.02010 =
         0.02869   -0.00210   -0.00058    0.00022
AFIX  43
H10B  2    0.453982   -0.165967    0.286210   -31.00000   -1.20000
AFIX   0
C11B  1    0.566684   -0.180628    0.480999   -31.00000    0.01983    0.02125 =
         0.03241   -0.00044    0.00730   -0.00235
C12B  1    0.681137   -0.150079    0.575317   -31.00000    0.02199    0.01678 =
         0.02187    0.00038    0.00603   -0.00042
AFIX  43
H12B  2    0.703248   -0.175821    0.663475   -31.00000   -1.20000
AFIX   0
PART 0
N1    3    0.879606   -0.054940    0.642953    11.00000    0.01772    0.01370 =
         0.01757    0.00059    0.00215   -0.00069
N2    3    1.039559    0.112021    0.746063    11.00000    0.01753    0.01373 =
         0.02359    0.00222   -0.00057   -0.00049
AFIX  93
H2A   2    1.082167    0.033775    0.796349    11.00000   -1.20000
H2B   2    1.070363    0.207933    0.754064    11.00000   -1.20000
AFIX   0
C13   1    0.926686    0.084861    0.656444    11.00000    0.01596    0.01402 =
         0.01519    0.00031    0.00507    0.00111
HKLF   4
 

END  
     

;

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 0.72813(15) 0.2259(2) 0.66086(17) 0.0259(3) Uani 0.5226(18) 1 d P A 1
C1A C 0.86428(11) 0.22971(16) 0.57940(12) 0.0155(3) Uani 0.5226(18) 1 d P A 1
C2A C 0.76671(12) 0.29305(17) 0.58741(13) 0.0184(3) Uani 0.5226(18) 1 d P A 1
C3A C 0.70754(12) 0.42641(17) 0.51631(14) 0.0213(3) Uani 0.5226(18) 1 d P A 1
H3A H 0.6410 0.4677 0.5232 0.026 Uiso 0.5226(18) 1 calc PR A 1
C4A C 0.74703(13) 0.49861(17) 0.43493(14) 0.0227(3) Uani 0.5226(18) 1 d P A 1
H4A H 0.7073 0.5901 0.3860 0.027 Uiso 0.5226(18) 1 calc PR A 1
C5A C 0.84407(14) 0.43819(17) 0.42468(14) 0.0224(3) Uani 0.5226(18) 1 d P A 1
H5A H 0.8708 0.4874 0.3687 0.027 Uiso 0.5226(18) 1 calc PR A 1
C6A C 0.90184(13) 0.30453(17) 0.49734(13) 0.0198(3) Uani 0.5226(18) 1 d P A 1
H6A H 0.9686 0.2635 0.4907 0.024 Uiso 0.5226(18) 1 calc PR A 1
F1B F 0.98646(17) 0.2393(2) 0.48083(19) 0.0259(3) Uani 0.4774(18) 1 d P A 2
C1B C 0.86428(11) 0.22971(16) 0.57940(12) 0.0155(3) Uani 0.4774(18) 1 d P A 2
C2B C 0.90184(13) 0.30453(17) 0.49734(13) 0.0198(3) Uani 0.4774(18) 1 d P A 2
C3B C 0.84407(14) 0.43819(17) 0.42468(14) 0.0224(3) Uani 0.4774(18) 1 d P A 2
H3B H 0.8708 0.4874 0.3687 0.027 Uiso 0.4774(18) 1 calc PR A 2
C4B C 0.74703(13) 0.49861(17) 0.43493(14) 0.0227(3) Uani 0.4774(18) 1 d P A 2
H4B H 0.7073 0.5901 0.3860 0.027 Uiso 0.4774(18) 1 calc PR A 2
C5B C 0.70754(12) 0.42641(17) 0.51631(14) 0.0213(3) Uani 0.4774(18) 1 d P A 2
H5B H 0.6410 0.4677 0.5232 0.026 Uiso 0.4774(18) 1 calc PR A 2
C6B C 0.76671(12) 0.29305(17) 0.58741(13) 0.0184(3) Uani 0.4774(18) 1 d P A 2
H6B H 0.7397 0.2437 0.6431 0.022 Uiso 0.4774(18) 1 calc PR A 2
F2A F 0.58317(10) -0.04573(14) 0.19539(10) 0.0310(3) Uani 0.893(2) 1 d P B 1
C7A C 0.76403(12) -0.08211(16) 0.54231(13) 0.0175(3) Uani 0.893(2) 1 d P B 1
C8A C 0.68114(13) -0.15008(17) 0.57532(14) 0.0217(3) Uani 0.893(2) 1 d P B 1
H8A H 0.7032 -0.1758 0.6635 0.026 Uiso 0.893(2) 1 calc PR B 1
C9A C 0.56668(13) -0.18063(19) 0.48100(16) 0.0262(3) Uani 0.893(2) 1 d P B 1
H9A H 0.5112 -0.2259 0.5056 0.031 Uiso 0.893(2) 1 calc PR B 1
C10A C 0.53224(13) -0.14597(19) 0.35130(16) 0.0271(3) Uani 0.893(2) 1 d P B 1
H10A H 0.4540 -0.1660 0.2862 0.033 Uiso 0.893(2) 1 calc PR B 1
C11A C 0.61589(14) -0.08166(18) 0.32104(14) 0.0245(3) Uani 0.893(2) 1 d P B 1
C12A C 0.73185(13) -0.05004(17) 0.41174(14) 0.0208(3) Uani 0.893(2) 1 d P B 1
H12A H 0.7873 -0.0080 0.3858 0.025 Uiso 0.893(2) 1 calc PR B 1
F2B F 0.4893(8) -0.2276(12) 0.4903(8) 0.0310(3) Uani 0.107(2) 1 d P B 2
C7B C 0.76403(12) -0.08211(16) 0.54231(13) 0.0175(3) Uani 0.107(2) 1 d P B 2
C8B C 0.73185(13) -0.05004(17) 0.41174(14) 0.0208(3) Uani 0.107(2) 1 d P B 2
H8B H 0.7873 -0.0080 0.3858 0.025 Uiso 0.107(2) 1 calc PR B 2
C9B C 0.61589(14) -0.08166(18) 0.32104(14) 0.0245(3) Uani 0.107(2) 1 d P B 2
H9B H 0.5932 -0.0571 0.2326 0.029 Uiso 0.107(2) 1 calc PR B 2
C10B C 0.53224(13) -0.14597(19) 0.35130(16) 0.0271(3) Uani 0.107(2) 1 d P B 2
H10B H 0.4540 -0.1660 0.2862 0.033 Uiso 0.107(2) 1 calc PR B 2
C11B C 0.56668(13) -0.18063(19) 0.48100(16) 0.0262(3) Uani 0.107(2) 1 d P B 2
C12B C 0.68114(13) -0.15008(17) 0.57532(14) 0.0217(3) Uani 0.107(2) 1 d P B 2
H12B H 0.7032 -0.1758 0.6635 0.026 Uiso 0.107(2) 1 calc PR B 2
N1 N 0.87961(10) -0.05494(14) 0.64295(11) 0.0186(3) Uani 1 1 d . . .
N2 N 1.03956(10) 0.11202(15) 0.74606(12) 0.0221(3) Uani 1 1 d . . .
H2A H 1.0822 0.0338 0.7963 0.026 Uiso 1 1 calc R B .
H2B H 1.0704 0.2079 0.7541 0.026 Uiso 1 1 calc R . .
C13 C 0.92669(11) 0.08486(16) 0.65644(12) 0.0158(3) Uani 1 1 d . A .


_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 1.286(2) . ?
C1A C6A 1.389(2) . ?
C1A C2A 1.3894(19) . ?
C1A C13 1.5007(18) . ?
C2A C3A 1.3881(19) . ?
C3A C4A 1.389(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.386(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.392(2) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
F2A C11A 1.3497(18) . ?
C7A C8A 1.394(2) . ?
C7A C12A 1.398(2) . ?
C7A N1 1.4171(17) . ?
C8A C9A 1.388(2) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.387(2) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.371(2) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.391(2) . ?
C12A H12A 0.9500 . ?
N1 C13 1.2919(18) . ?
N2 C13 1.3530(17) . ?
N2 H2A 0.8800 . ?
N2 H2B 0.8800 . ?

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 117.80(12) . . ?
C6A C1A C13 121.12(12) . . ?
C2A C1A C13 121.08(12) . . ?
F1A C2A C3A 118.44(14) . . ?
F1A C2A C1A 119.71(14) . . ?
C3A C2A C1A 121.85(13) . . ?
C2A C3A C4A 119.07(14) . . ?
C2A C3A H3A 120.5 . . ?
C4A C3A H3A 120.5 . . ?
C5A C4A C3A 120.48(13) . . ?
C5A C4A H4A 119.8 . . ?
C3A C4A H4A 119.8 . . ?
C4A C5A C6A 119.20(14) . . ?
C4A C5A H5A 120.4 . . ?
C6A C5A H5A 120.4 . . ?
C1A C6A C5A 121.60(14) . . ?
C1A C6A H6A 119.2 . . ?
C5A C6A H6A 119.2 . . ?
C8A C7A C12A 119.12(13) . . ?
C8A C7A N1 118.10(12) . . ?
C12A C7A N1 122.72(13) . . ?
C9A C8A C7A 120.84(14) . . ?
C9A C8A H8A 119.6 . . ?
C7A C8A H8A 119.6 . . ?
C10A C9A C8A 120.87(15) . . ?
C10A C9A H9A 119.6 . . ?
C8A C9A H9A 119.6 . . ?
C11A C10A C9A 117.18(14) . . ?
C11A C10A H10A 121.4 . . ?
C9A C10A H10A 121.4 . . ?
F2A C11A C10A 117.78(13) . . ?
F2A C11A C12A 118.09(15) . . ?
C10A C11A C12A 124.13(14) . . ?
C11A C12A C7A 117.81(14) . . ?
C11A C12A H12A 121.1 . . ?
C7A C12A H12A 121.1 . . ?
C13 N1 C7A 119.66(11) . . ?
C13 N2 H2A 120.0 . . ?
C13 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C13 N2 121.09(12) . . ?
N1 C13 C1A 124.79(12) . . ?
N2 C13 C1A 114.11(11) . . ?

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 179.00(15) . . . . ?
C13 C1A C2A F1A -0.7(2) . . . . ?
C6A C1A C2A C3A 0.1(2) . . . . ?
C13 C1A C2A C3A -179.64(12) . . . . ?
F1A C2A C3A C4A -178.95(15) . . . . ?
C1A C2A C3A C4A 0.0(2) . . . . ?
C2A C3A C4A C5A 0.1(2) . . . . ?
C3A C4A C5A C6A -0.2(2) . . . . ?
C2A C1A C6A C5A -0.3(2) . . . . ?
C13 C1A C6A C5A 179.50(13) . . . . ?
C4A C5A C6A C1A 0.3(2) . . . . ?
C12A C7A C8A C9A -2.3(2) . . . . ?
N1 C7A C8A C9A -179.57(14) . . . . ?
C7A C8A C9A C10A 0.7(2) . . . . ?
C8A C9A C10A C11A 0.3(2) . . . . ?
C9A C10A C11A F2A -179.28(14) . . . . ?
C9A C10A C11A C12A 0.2(2) . . . . ?
F2A C11A C12A C7A 177.73(13) . . . . ?
C10A C11A C12A C7A -1.7(2) . . . . ?
C8A C7A C12A C11A 2.7(2) . . . . ?
N1 C7A C12A C11A 179.86(13) . . . . ?
C8A C7A N1 C13 -127.82(15) . . . . ?
C12A C7A N1 C13 55.02(19) . . . . ?
C7A N1 C13 N2 -175.67(13) . . . . ?
C7A N1 C13 C1A 5.4(2) . . . . ?
C6A C1A C13 N1 -116.66(16) . . . . ?
C2A C1A C13 N1 63.08(19) . . . . ?
C6A C1A C13 N2 64.37(17) . . . . ?
C2A C1A C13 N2 -115.89(15) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.57
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_DZ
_database_code_depnum_ccdc_archive 'CCDC 1016405'
_audit_update_record             
;
2014-07-28 deposited with the CCDC.
2015-03-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   6.7821(4)
_cell_length_b                   22.9709(13)
_cell_length_c                   6.9552(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.464(4)
_cell_angle_gamma                90.00
_cell_volume                     1083.20(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      30.41

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_absorpt_coefficient_mu    0.110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9783
_exptl_absorpt_correction_T_max  0.9891
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10701
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0275
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         28.28
_reflns_number_total             2672
_reflns_number_gt                2173
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0437P)²+0.4845P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2672
_refine_ls_number_parameters     162
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0541
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1044
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_iucr_refine_instruction_details 
;
TITL DB12_P in P2(1)/n
CELL 0.71073 6.7821 22.9709 6.9552 90.000 91.464 90.000
ZERR 4.00 0.0004 0.0013 0.0004 0.000 0.004 0.000
LATT 1
SYMM -x+1/2, y+1/2, -z+1/2
SFAC C H N F
UNIT 52 40 8 8
MERG 2
L.S. 12
ACTA
BOND $H
HTAB
CONF
SIZE 0.2 0.2 0.1
TEMP -173
EADP F1A F1B
EADP F2A F2B
EXYZ C1A C1B
EXYZ C2A C6B
EXYZ C3A C5B
EXYZ C4A C4B
EXYZ C5A C3B
EXYZ C6A C2B
EADP C1A C1B
EADP C2A C6B
EADP C3A C5B
EADP C4A C4B
EADP C5A C3B
EADP C6A C2B
EXYZ C7A C7B
EXYZ C8A C12B
EXYZ C9A C11B
EXYZ C10A C10B
EXYZ C11A C9B
EXYZ C12A C8B
EADP C7A C7B
EADP C8A C12B
EADP C9A C11B
EADP C10A C10B
EADP C11A C9B
EADP C12A C8B
FMAP 2
PLAN 5
WGHT    0.043700    0.484500
FVAR       0.17329   0.96589   0.87380
PART 1
F1A   4   -0.424165    0.191087    0.340887    21.00000    0.01881    0.03304 =
         0.04352   -0.00305   -0.00300    0.00045
C1A   1   -0.078855    0.191407    0.389829    21.00000    0.02199    0.02095 =
         0.01606    0.00002    0.00504   -0.00068
C2A   1    0.093446    0.158258    0.408854    21.00000    0.02282    0.02520 =
         0.02456    0.00108    0.00478    0.00068
AFIX  43
H2A   2    0.216544    0.177334    0.428903    21.00000   -1.20000
AFIX   0
C3A   1    0.087559    0.098067    0.398944    21.00000    0.03201    0.02513 =
         0.03143    0.00142    0.00533    0.00635
AFIX  43
H3A   2    0.205856    0.076215    0.414162    21.00000   -1.20000
AFIX   0
C4A   1   -0.090204    0.069676    0.366932    21.00000    0.04194    0.02092 =
         0.02721   -0.00147    0.00594   -0.00164
AFIX  43
H4A   2   -0.093425    0.028419    0.357928    21.00000   -1.20000
AFIX   0
C5A   1   -0.262976    0.101234    0.348048    21.00000    0.03168    0.02948 =
         0.02449   -0.00465    0.00387   -0.00982
AFIX  43
H5A   2   -0.385695    0.082071    0.326533    21.00000   -1.20000
AFIX   0
C6A   1   -0.253930    0.161239    0.361051    21.00000    0.02089    0.02779 =
         0.01970   -0.00097    0.00242   -0.00090
PART 2
F1B   4    0.234048    0.178902    0.453449   -21.00000    0.01881    0.03304 =
         0.04352   -0.00305   -0.00300    0.00045
C1B   1   -0.078855    0.191407    0.389829   -21.00000    0.02199    0.02095 =
         0.01606    0.00002    0.00504   -0.00068
C2B   1   -0.253930    0.161239    0.361051   -21.00000    0.02089    0.02779 =
         0.01970   -0.00097    0.00242   -0.00090
AFIX  43
H2B   2   -0.373275    0.182761    0.349727   -21.00000   -1.20000
AFIX   0
C3B   1   -0.262976    0.101234    0.348048   -21.00000    0.03168    0.02948 =
         0.02449   -0.00465    0.00387   -0.00982
AFIX  43
H3B   2   -0.385695    0.082071    0.326533   -21.00000   -1.20000
AFIX   0
C4B   1   -0.090204    0.069676    0.366932   -21.00000    0.04194    0.02092 =
         0.02721   -0.00147    0.00594   -0.00164
AFIX  43
H4B   2   -0.093425    0.028419    0.357928   -21.00000   -1.20000
AFIX   0
C5B   1    0.087559    0.098067    0.398944   -21.00000    0.03201    0.02513 =
         0.03143    0.00142    0.00533    0.00635
AFIX  43
H5B   2    0.205856    0.076215    0.414162   -21.00000   -1.20000
AFIX   0
C6B   1    0.093446    0.158258    0.408854   -21.00000    0.02282    0.02520 =
         0.02456    0.00108    0.00478    0.00068
PART 0
PART 1
F2A   4    0.543295    0.432705    0.400641    31.00000    0.02614    0.03834 =
         0.04349   -0.00620    0.00420   -0.01195
C7A   1    0.115569    0.340551    0.327959    31.00000    0.02346    0.02113 =
         0.01758   -0.00095    0.00666   -0.00211
C8A   1   -0.028149    0.383615    0.298241    31.00000    0.02534    0.02467 =
         0.02627    0.00113    0.00348   -0.00146
AFIX  43
H8A   2   -0.161192    0.372817    0.271149    31.00000   -1.20000
AFIX   0
C9A   1    0.023207    0.441905    0.308250    31.00000    0.03982    0.02309 =
         0.03143    0.00451    0.00461    0.00295
AFIX  43
H9A   2   -0.076057    0.470665    0.289319    31.00000   -1.20000
AFIX   0
C10A  1    0.216028    0.459187    0.345241    31.00000    0.04229    0.02268 =
         0.02727   -0.00280    0.01010   -0.00733
AFIX  43
H10A  2    0.250871    0.499183    0.353455    31.00000   -1.20000
AFIX   0
C11A  1    0.354906    0.416083    0.369579    31.00000    0.02771    0.03316 =
         0.02342   -0.00506    0.00785   -0.01241
C12A  1    0.311593    0.357448    0.361639    31.00000    0.02358    0.02700 =
         0.02114   -0.00159    0.00703   -0.00187
AFIX  43
H12A  2    0.412691    0.329151    0.378673    31.00000   -1.20000
AFIX   0
PART 2
F2B   4   -0.075781    0.480016    0.248961   -31.00000    0.02614    0.03834 =
         0.04349   -0.00620    0.00420   -0.01195
C7B   1    0.115569    0.340551    0.327959   -31.00000    0.02346    0.02113 =
         0.01758   -0.00095    0.00666   -0.00211
C8B   1    0.311593    0.357448    0.361639   -31.00000    0.02358    0.02700 =
         0.02114   -0.00159    0.00703   -0.00187
AFIX  43
H8B   2    0.412691    0.329151    0.378673   -31.00000   -1.20000
AFIX   0
C9B   1    0.354906    0.416083    0.369579   -31.00000    0.02771    0.03316 =
         0.02342   -0.00506    0.00785   -0.01241
AFIX  43
H9B   2    0.488170    0.427288    0.393189   -31.00000   -1.20000
AFIX   0
C10B  1    0.216028    0.459187    0.345241   -31.00000    0.04229    0.02268 =
         0.02727   -0.00280    0.01010   -0.00733
AFIX  43
H10B  2    0.250871    0.499183    0.353455   -31.00000   -1.20000
AFIX   0
C11B  1    0.023207    0.441905    0.308250   -31.00000    0.03982    0.02309 =
         0.03143    0.00451    0.00461    0.00295
C12B  1   -0.028149    0.383615    0.298241   -31.00000    0.02534    0.02467 =
         0.02627    0.00113    0.00348   -0.00146
AFIX  43
H12B  2   -0.161192    0.372817    0.271149   -31.00000   -1.20000
AFIX   0
PART 0
N1    3    0.079023    0.280173    0.313989    11.00000    0.02026    0.02059 =
         0.02290   -0.00095    0.00589   -0.00079
N2    3   -0.201189    0.282697    0.512089    11.00000    0.02342    0.01973 =
         0.02749   -0.00157    0.01072   -0.00118
AFIX  93
H2C   2   -0.196994    0.320656    0.528748    11.00000   -1.20000
H2D   2   -0.293696    0.261994    0.566365    11.00000   -1.20000
AFIX   0
C13   1   -0.065769    0.256235    0.403315    11.00000    0.01789    0.02192 =
         0.01681    0.00010    0.00106    0.00086
HKLF   4

END  
     
;

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F -0.42417(12) 0.19109(4) 0.34089(14) 0.0319(3) Uani 0.966(2) 1 d P A 1
C1A C -0.07886(19) 0.19141(6) 0.38983(17) 0.0196(3) Uani 0.966(2) 1 d P A 1
C2A C 0.0934(2) 0.15826(6) 0.40885(19) 0.0241(3) Uani 0.966(2) 1 d P A 1
H2A H 0.2165 0.1773 0.4289 0.029 Uiso 0.966(2) 1 calc PR A 1
C3A C 0.0876(2) 0.09807(6) 0.3989(2) 0.0294(3) Uani 0.966(2) 1 d P A 1
H3A H 0.2059 0.0762 0.4142 0.035 Uiso 0.966(2) 1 calc PR A 1
C4A C -0.0902(2) 0.06968(6) 0.3669(2) 0.0299(3) Uani 0.966(2) 1 d P A 1
H4A H -0.0934 0.0284 0.3579 0.036 Uiso 0.966(2) 1 calc PR A 1
C5A C -0.2630(2) 0.10123(6) 0.3480(2) 0.0285(3) Uani 0.966(2) 1 d P A 1
H5A H -0.3857 0.0821 0.3265 0.034 Uiso 0.966(2) 1 calc PR A 1
C6A C -0.25393(19) 0.16124(6) 0.36105(18) 0.0228(3) Uani 0.966(2) 1 d P A 1
F1B F 0.234(3) 0.1789(11) 0.453(4) 0.0319(3) Uani 0.034(2) 1 d P A 2
C1B C -0.07886(19) 0.19141(6) 0.38983(17) 0.0196(3) Uani 0.034(2) 1 d P A 2
C2B C -0.25393(19) 0.16124(6) 0.36105(18) 0.0228(3) Uani 0.034(2) 1 d P A 2
H2B H -0.3733 0.1828 0.3497 0.027 Uiso 0.034(2) 1 calc PR A 2
C3B C -0.2630(2) 0.10123(6) 0.3480(2) 0.0285(3) Uani 0.034(2) 1 d P A 2
H3B H -0.3857 0.0821 0.3265 0.034 Uiso 0.034(2) 1 calc PR A 2
C4B C -0.0902(2) 0.06968(6) 0.3669(2) 0.0299(3) Uani 0.034(2) 1 d P A 2
H4B H -0.0934 0.0284 0.3579 0.036 Uiso 0.034(2) 1 calc PR A 2
C5B C 0.0876(2) 0.09807(6) 0.3989(2) 0.0294(3) Uani 0.034(2) 1 d P A 2
H5B H 0.2059 0.0762 0.4142 0.035 Uiso 0.034(2) 1 calc PR A 2
C6B C 0.0934(2) 0.15826(6) 0.40885(19) 0.0241(3) Uani 0.034(2) 1 d P A 2
F2A F 0.54330(14) 0.43271(5) 0.40064(15) 0.0359(3) Uani 0.8738(19) 1 d P B 1
C7A C 0.11557(19) 0.34055(6) 0.32796(18) 0.0206(3) Uani 0.8738(19) 1 d P B 1
C8A C -0.0281(2) 0.38362(6) 0.2982(2) 0.0254(3) Uani 0.8738(19) 1 d P B 1
H8A H -0.1612 0.3728 0.2711 0.030 Uiso 0.8738(19) 1 calc PR B 1
C9A C 0.0232(2) 0.44190(6) 0.3083(2) 0.0314(3) Uani 0.8738(19) 1 d P B 1
H9A H -0.0761 0.4707 0.2893 0.038 Uiso 0.8738(19) 1 calc PR B 1
C10A C 0.2160(2) 0.45919(6) 0.3452(2) 0.0306(3) Uani 0.8738(19) 1 d P B 1
H10A H 0.2509 0.4992 0.3535 0.037 Uiso 0.8738(19) 1 calc PR B 1
C11A C 0.3549(2) 0.41608(7) 0.3696(2) 0.0280(3) Uani 0.8738(19) 1 d P B 1
C12A C 0.3116(2) 0.35745(6) 0.36164(19) 0.0238(3) Uani 0.8738(19) 1 d P B 1
H12A H 0.4127 0.3292 0.3787 0.029 Uiso 0.8738(19) 1 calc PR B 1
F2B F -0.0758(10) 0.4800(3) 0.2490(11) 0.0359(3) Uani 0.1262(19) 1 d P B 2
C7B C 0.11557(19) 0.34055(6) 0.32796(18) 0.0206(3) Uani 0.1262(19) 1 d P B 2
C8B C 0.3116(2) 0.35745(6) 0.36164(19) 0.0238(3) Uani 0.1262(19) 1 d P B 2
H8B H 0.4127 0.3292 0.3787 0.029 Uiso 0.1262(19) 1 calc PR B 2
C9B C 0.3549(2) 0.41608(7) 0.3696(2) 0.0280(3) Uani 0.1262(19) 1 d P B 2
H9B H 0.4882 0.4273 0.3932 0.034 Uiso 0.1262(19) 1 calc PR B 2
C10B C 0.2160(2) 0.45919(6) 0.3452(2) 0.0306(3) Uani 0.1262(19) 1 d P B 2
H10B H 0.2509 0.4992 0.3535 0.037 Uiso 0.1262(19) 1 calc PR B 2
C11B C 0.0232(2) 0.44190(6) 0.3083(2) 0.0314(3) Uani 0.1262(19) 1 d P B 2
C12B C -0.0281(2) 0.38362(6) 0.2982(2) 0.0254(3) Uani 0.1262(19) 1 d P B 2
H12B H -0.1612 0.3728 0.2711 0.030 Uiso 0.1262(19) 1 calc PR B 2
N1 N 0.07902(16) 0.28017(5) 0.31399(16) 0.0212(2) Uani 1 1 d . . .
N2 N -0.20119(16) 0.28270(5) 0.51209(16) 0.0234(3) Uani 1 1 d . . .
H2C H -0.1970 0.3207 0.5287 0.028 Uiso 1 1 calc R B .
H2D H -0.2937 0.2620 0.5664 0.028 Uiso 1 1 calc R . .
C13 C -0.06577(18) 0.25623(6) 0.40331(17) 0.0189(3) Uani 1 1 d . A .


_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 C6A 1.3470(16) . ?
C1A C6A 1.3849(18) . ?
C1A C2A 1.3982(18) . ?
C1A C13 1.4946(18) . ?
C2A C3A 1.385(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.384(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.381(2) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.383(2) . ?
C5A H5A 0.9500 . ?
F2A C11A 1.3457(17) . ?
C7A C12A 1.3989(19) . ?
C7A C8A 1.4004(19) . ?
C7A N1 1.4118(17) . ?
C8A C9A 1.385(2) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.384(2) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.374(2) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.379(2) . ?
C12A H12A 0.9500 . ?
N1 C13 1.2976(16) . ?
N2 C13 1.3494(15) . ?
N2 H2C 0.8800 . ?
N2 H2D 0.8800 . ?

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 116.91(12) . . ?
C6A C1A C13 123.84(12) . . ?
C2A C1A C13 119.24(12) . . ?
C3A C2A C1A 121.07(13) . . ?
C3A C2A H2A 119.5 . . ?
C1A C2A H2A 119.5 . . ?
C4A C3A C2A 120.16(14) . . ?
C4A C3A H3A 119.9 . . ?
C2A C3A H3A 119.9 . . ?
C5A C4A C3A 120.10(13) . . ?
C5A C4A H4A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C4A C5A C6A 118.74(13) . . ?
C4A C5A H5A 120.6 . . ?
C6A C5A H5A 120.6 . . ?
F1A C6A C5A 117.66(12) . . ?
F1A C6A C1A 119.32(12) . . ?
C5A C6A C1A 123.01(13) . . ?
C12A C7A C8A 118.92(12) . . ?
C12A C7A N1 116.65(12) . . ?
C8A C7A N1 124.30(12) . . ?
C9A C8A C7A 120.16(14) . . ?
C9A C8A H8A 119.9 . . ?
C7A C8A H8A 119.9 . . ?
C10A C9A C8A 121.45(14) . . ?
C10A C9A H9A 119.3 . . ?
C8A C9A H9A 119.3 . . ?
C11A C10A C9A 117.23(13) . . ?
C11A C10A H10A 121.4 . . ?
C9A C10A H10A 121.4 . . ?
F2A C11A C10A 117.41(13) . . ?
F2A C11A C12A 118.94(14) . . ?
C10A C11A C12A 123.65(14) . . ?
C11A C12A C7A 118.56(13) . . ?
C11A C12A H12A 120.7 . . ?
C7A C12A H12A 120.7 . . ?
C13 N1 C7A 121.13(11) . . ?
C13 N2 H2C 120.0 . . ?
C13 N2 H2D 120.0 . . ?
H2C N2 H2D 120.0 . . ?
N1 C13 N2 127.72(12) . . ?
N1 C13 C1A 115.89(11) . . ?
N2 C13 C1A 116.35(11) . . ?

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 0.06(19) . . . . ?
C13 C1A C2A C3A 179.43(12) . . . . ?
C1A C2A C3A C4A 1.0(2) . . . . ?
C2A C3A C4A C5A -1.1(2) . . . . ?
C3A C4A C5A C6A 0.2(2) . . . . ?
C4A C5A C6A F1A 179.56(12) . . . . ?
C4A C5A C6A C1A 0.8(2) . . . . ?
C2A C1A C6A F1A -179.68(11) . . . . ?
C13 C1A C6A F1A 0.98(19) . . . . ?
C2A C1A C6A C5A -0.98(19) . . . . ?
C13 C1A C6A C5A 179.68(12) . . . . ?
C12A C7A C8A C9A -1.99(19) . . . . ?
N1 C7A C8A C9A -177.65(12) . . . . ?
C7A C8A C9A C10A 0.7(2) . . . . ?
C8A C9A C10A C11A 0.7(2) . . . . ?
C9A C10A C11A F2A 178.33(12) . . . . ?
C9A C10A C11A C12A -0.9(2) . . . . ?
F2A C11A C12A C7A -179.56(11) . . . . ?
C10A C11A C12A C7A -0.3(2) . . . . ?
C8A C7A C12A C11A 1.78(18) . . . . ?
N1 C7A C12A C11A 177.76(11) . . . . ?
C12A C7A N1 C13 134.17(13) . . . . ?
C8A C7A N1 C13 -50.09(18) . . . . ?
C7A N1 C13 N2 2.2(2) . . . . ?
C7A N1 C13 C1A -175.23(12) . . . . ?
C6A C1A C13 N1 -138.10(13) . . . . ?
C2A C1A C13 N1 42.57(17) . . . . ?
C6A C1A C13 N2 44.15(18) . . . . ?
C2A C1A C13 N2 -135.18(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        28.28
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.313
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.046
