# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_bpk-069
_database_code_depnum_ccdc_archive 'CCDC 1487669'
_audit_update_record             
;
2016-06-25 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
6-methyl-3-(pyridin-2-yl)-[1,2,4]triazolo[4,3-a]pyridine
_chemical_name_common            ?
_chemical_melting_point          447.15
_chemical_formula_moiety         C12H10N4
_chemical_formula_sum            'C12 H10 N4'
_chemical_formula_weight         210.24

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'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5325(7)
_cell_length_b                   8.2606(7)
_cell_length_c                   9.0301(8)
_cell_angle_alpha                73.705(8)
_cell_angle_beta                 83.998(8)
_cell_angle_gamma                68.210(8)
_cell_volume                     500.78(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2246
_cell_measurement_theta_min      3.74
_cell_measurement_theta_max      25.24

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             220
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'CCD area detector'
_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            2839
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         25.24
_reflns_number_total             1792
_reflns_number_gt                1440
_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)+(0.0320P)²+0.0573P] 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         1792
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0493
_refine_ls_wR_factor_ref         0.1054
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.165
_refine_ls_restrained_S_all      1.165
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.66665(19) 0.55408(18) 0.35169(15) 0.0343(4) Uani 1 1 d . . .
N4 N 0.8203(2) 0.4761(2) 0.65773(16) 0.0439(4) Uani 1 1 d . . .
N3 N 0.8268(2) 0.2716(2) 0.34968(18) 0.0531(5) Uani 1 1 d . . .
N2 N 0.7307(3) 0.3562(2) 0.21230(18) 0.0573(5) Uani 1 1 d . . .
C7 C 0.8689(2) 0.3440(2) 0.58646(19) 0.0367(4) Uani 1 1 d . . .
C6 C 0.7897(2) 0.3885(2) 0.43277(19) 0.0377(4) Uani 1 1 d . . .
C5 C 0.5809(2) 0.7204(2) 0.38388(19) 0.0389(4) Uani 1 1 d . . .
H5 H 0.6030 0.7352 0.4778 0.047 Uiso 1 1 calc R . .
C1 C 0.4654(3) 0.8607(2) 0.2784(2) 0.0409(5) Uani 1 1 d . . .
C3 C 0.5154(3) 0.6727(3) 0.1035(2) 0.0479(5) Uani 1 1 d . . .
H3 H 0.4923 0.6584 0.0097 0.057 Uiso 1 1 calc R . .
C2 C 0.4342(3) 0.8342(2) 0.1362(2) 0.0456(5) Uani 1 1 d . . .
H2 H 0.3551 0.9313 0.0630 0.055 Uiso 1 1 calc R . .
C8 C 0.9881(3) 0.1682(2) 0.6522(2) 0.0448(5) Uani 1 1 d . . .
H8 H 1.0200 0.0801 0.5987 0.054 Uiso 1 1 calc R . .
C4 C 0.6357(3) 0.5264(2) 0.21400(19) 0.0411(5) Uani 1 1 d . . .
C11 C 0.8918(3) 0.4310(3) 0.7991(2) 0.0504(5) Uani 1 1 d . . .
H11 H 0.8602 0.5210 0.8505 0.060 Uiso 1 1 calc R . .
C10 C 1.0086(3) 0.2604(3) 0.8731(2) 0.0515(5) Uani 1 1 d . . .
H10 H 1.0534 0.2358 0.9721 0.062 Uiso 1 1 calc R . .
C9 C 1.0579(3) 0.1272(3) 0.7977(2) 0.0506(5) Uani 1 1 d . . .
H9 H 1.1377 0.0104 0.8446 0.061 Uiso 1 1 calc R . .
C12 C 0.3697(3) 1.0425(3) 0.3099(2) 0.0636(6) Uani 1 1 d . . .
H12A H 0.3536 1.0279 0.4192 0.095 Uiso 1 1 calc R . .
H12B H 0.2469 1.1012 0.2605 0.095 Uiso 1 1 calc R . .
H12C H 0.4473 1.1147 0.2702 0.095 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0387(8) 0.0334(8) 0.0320(8) -0.0107(6) 0.0009(6) -0.0132(6)
N4 0.0510(10) 0.0398(9) 0.0385(9) -0.0096(7) -0.0057(7) -0.0125(7)
N3 0.0683(12) 0.0399(9) 0.0454(10) -0.0175(7) -0.0055(8) -0.0068(8)
N2 0.0786(13) 0.0472(10) 0.0429(10) -0.0191(8) -0.0087(9) -0.0115(9)
C7 0.0380(10) 0.0362(10) 0.0355(10) -0.0084(8) 0.0015(8) -0.0139(8)
C6 0.0404(10) 0.0312(10) 0.0385(10) -0.0094(8) 0.0008(8) -0.0097(8)
C5 0.0441(11) 0.0354(10) 0.0395(10) -0.0127(8) -0.0029(8) -0.0138(8)
C1 0.0413(11) 0.0356(10) 0.0441(11) -0.0067(8) -0.0056(8) -0.0134(8)
C3 0.0572(13) 0.0536(13) 0.0349(10) -0.0096(9) -0.0073(9) -0.0214(10)
C2 0.0480(12) 0.0435(12) 0.0418(11) -0.0020(8) -0.0129(9) -0.0160(9)
C8 0.0448(11) 0.0368(11) 0.0473(11) -0.0102(8) -0.0022(9) -0.0084(8)
C4 0.0503(12) 0.0421(11) 0.0341(10) -0.0146(8) -0.0014(8) -0.0163(9)
C11 0.0573(13) 0.0510(12) 0.0442(11) -0.0154(9) -0.0064(9) -0.0171(10)
C10 0.0501(12) 0.0583(13) 0.0425(11) -0.0057(10) -0.0107(9) -0.0181(10)
C9 0.0438(12) 0.0435(12) 0.0522(12) -0.0013(9) -0.0096(9) -0.0076(9)
C12 0.0727(15) 0.0407(12) 0.0677(14) -0.0128(10) -0.0194(12) -0.0052(11)

_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
N1 C6 1.380(2) . ?
N1 C4 1.383(2) . ?
N1 C5 1.384(2) . ?
N4 C11 1.336(2) . ?
N4 C7 1.337(2) . ?
N3 C6 1.318(2) . ?
N3 N2 1.370(2) . ?
N2 C4 1.324(2) . ?
C7 C8 1.388(2) . ?
C7 C6 1.463(2) . ?
C5 C1 1.346(2) . ?
C5 H5 0.9300 . ?
C1 C2 1.418(2) . ?
C1 C12 1.500(2) . ?
C3 C2 1.348(2) . ?
C3 C4 1.406(2) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C8 C9 1.370(2) . ?
C8 H8 0.9300 . ?
C11 C10 1.371(3) . ?
C11 H11 0.9300 . ?
C10 C9 1.370(3) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N1 C4 104.63(14) . . ?
C6 N1 C5 133.50(14) . . ?
C4 N1 C5 121.87(14) . . ?
C11 N4 C7 116.49(16) . . ?
C6 N3 N2 109.26(15) . . ?
C4 N2 N3 106.77(14) . . ?
N4 C7 C8 123.07(16) . . ?
N4 C7 C6 117.74(15) . . ?
C8 C7 C6 119.19(16) . . ?
N3 C6 N1 109.09(15) . . ?
N3 C6 C7 123.93(16) . . ?
N1 C6 C7 126.98(15) . . ?
C1 C5 N1 119.60(15) . . ?
C1 C5 H5 120.2 . . ?
N1 C5 H5 120.2 . . ?
C5 C1 C2 118.99(17) . . ?
C5 C1 C12 120.93(16) . . ?
C2 C1 C12 120.09(16) . . ?
C2 C3 C4 118.78(17) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C2 C1 122.14(17) . . ?
C3 C2 H2 118.9 . . ?
C1 C2 H2 118.9 . . ?
C9 C8 C7 118.64(18) . . ?
C9 C8 H8 120.7 . . ?
C7 C8 H8 120.7 . . ?
N2 C4 N1 110.25(15) . . ?
N2 C4 C3 131.12(16) . . ?
N1 C4 C3 118.62(16) . . ?
N4 C11 C10 124.20(18) . . ?
N4 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
C9 C10 C11 118.41(18) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C10 C9 C8 119.19(18) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
C1 C12 H12A 109.5 . . ?
C1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N3 N2 C4 0.2(2) . . . . ?
C11 N4 C7 C8 -0.5(3) . . . . ?
C11 N4 C7 C6 178.80(16) . . . . ?
N2 N3 C6 N1 0.3(2) . . . . ?
N2 N3 C6 C7 -179.96(16) . . . . ?
C4 N1 C6 N3 -0.62(19) . . . . ?
C5 N1 C6 N3 179.06(17) . . . . ?
C4 N1 C6 C7 179.61(16) . . . . ?
C5 N1 C6 C7 -0.7(3) . . . . ?
N4 C7 C6 N3 179.59(16) . . . . ?
C8 C7 C6 N3 -1.1(3) . . . . ?
N4 C7 C6 N1 -0.7(3) . . . . ?
C8 C7 C6 N1 178.63(15) . . . . ?
C6 N1 C5 C1 179.69(17) . . . . ?
C4 N1 C5 C1 -0.7(2) . . . . ?
N1 C5 C1 C2 0.0(3) . . . . ?
N1 C5 C1 C12 179.76(16) . . . . ?
C4 C3 C2 C1 -0.4(3) . . . . ?
C5 C1 C2 C3 0.5(3) . . . . ?
C12 C1 C2 C3 -179.24(18) . . . . ?
N4 C7 C8 C9 0.7(3) . . . . ?
C6 C7 C8 C9 -178.52(17) . . . . ?
N3 N2 C4 N1 -0.6(2) . . . . ?
N3 N2 C4 C3 179.66(19) . . . . ?
C6 N1 C4 N2 0.8(2) . . . . ?
C5 N1 C4 N2 -178.94(15) . . . . ?
C6 N1 C4 C3 -179.48(15) . . . . ?
C5 N1 C4 C3 0.8(2) . . . . ?
C2 C3 C4 N2 179.41(19) . . . . ?
C2 C3 C4 N1 -0.3(3) . . . . ?
C7 N4 C11 C10 -0.3(3) . . . . ?
N4 C11 C10 C9 0.8(3) . . . . ?
C11 C10 C9 C8 -0.5(3) . . . . ?
C7 C8 C9 C10 -0.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.033
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method MeOH/DCM
_chemical_compound_source        'Synthesized compound'
_chemical_properties_physical    ', Heat-sensitive'
####################################################################### 
# 
# 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_ra-070
_database_code_depnum_ccdc_archive 'CCDC 1487670'
_audit_update_record             
;
2016-06-25 deposited with the CCDC.
2016-10-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
6-fluoro-3-phenyl-[1,2,4]triazolo[4,3-a]pyridine
_chemical_name_common            ?
_chemical_melting_point          435.15
_chemical_formula_moiety         C12H8FN3
_chemical_formula_sum            'C12 H8 F N3'
_chemical_formula_weight         213.21

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           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   6.5842(10)
_cell_length_b                   10.527(3)
_cell_length_c                   14.581(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1010.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1803
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      24.76

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             440
_exptl_absorpt_coefficient_mu    0.100
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'CCD area detector'
_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            2534
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_av_sigmaI/netI    0.0469
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.40
_diffrn_reflns_theta_max         25.25
_reflns_number_total             1422
_reflns_number_gt                1088
_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)+(0.0016P)²+0.5613P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   1(2)
_refine_ls_number_reflns         1422
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0634
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.0765
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F2 F 0.3002(3) 0.6169(2) 0.59849(13) 0.0666(6) Uani 1 1 d . . .
N1 N 0.6653(4) 0.6072(2) 0.41802(16) 0.0413(6) Uani 1 1 d . . .
N3 N 0.9206(4) 0.5931(3) 0.3209(2) 0.0573(8) Uani 1 1 d . . .
N2 N 0.9915(4) 0.5542(3) 0.40520(19) 0.0591(8) Uani 1 1 d . . .
C6 C 0.7256(5) 0.6248(3) 0.3289(2) 0.0449(8) Uani 1 1 d . . .
C7 C 0.6037(5) 0.6776(3) 0.2533(2) 0.0453(8) Uani 1 1 d . . .
C1 C 0.4817(5) 0.6269(3) 0.4621(2) 0.0433(8) Uani 1 1 d . . .
H1 H 0.3674 0.6558 0.4310 0.052 Uiso 1 1 calc R . .
C12 C 0.4001(5) 0.6435(3) 0.2382(2) 0.0504(9) Uani 1 1 d . . .
H12 H 0.3347 0.5879 0.2781 0.060 Uiso 1 1 calc R . .
C2 C 0.4780(5) 0.6014(3) 0.5533(2) 0.0479(8) Uani 1 1 d . . .
C5 C 0.8374(5) 0.5641(3) 0.4626(2) 0.0471(8) Uani 1 1 d . . .
C11 C 0.2972(6) 0.6934(4) 0.1632(2) 0.0618(11) Uani 1 1 d . . .
H11 H 0.1627 0.6705 0.1528 0.074 Uiso 1 1 calc R . .
C8 C 0.6958(6) 0.7630(3) 0.1927(2) 0.0544(9) Uani 1 1 d . . .
H8 H 0.8300 0.7872 0.2023 0.065 Uiso 1 1 calc R . .
C4 C 0.8247(5) 0.5392(3) 0.5590(2) 0.0556(9) Uani 1 1 d . . .
H4 H 0.9380 0.5107 0.5911 0.067 Uiso 1 1 calc R . .
C3 C 0.6454(5) 0.5578(3) 0.6032(2) 0.0558(9) Uani 1 1 d . . .
H3 H 0.6342 0.5416 0.6657 0.067 Uiso 1 1 calc R . .
C10 C 0.3919(6) 0.7765(3) 0.1039(3) 0.0655(11) Uani 1 1 d . . .
H10 H 0.3217 0.8088 0.0538 0.079 Uiso 1 1 calc R . .
C9 C 0.5916(6) 0.8117(3) 0.1192(3) 0.0640(11) Uani 1 1 d . . .
H9 H 0.6552 0.8684 0.0796 0.077 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
F2 0.0673(12) 0.0785(14) 0.0541(11) -0.0010(12) 0.0205(11) 0.0100(12)
N1 0.0405(13) 0.0411(14) 0.0424(15) -0.0001(14) -0.0004(13) 0.0014(14)
N3 0.0412(15) 0.079(2) 0.0518(17) 0.0003(19) 0.0023(14) 0.0047(17)
N2 0.0418(15) 0.079(2) 0.0563(17) 0.0031(19) -0.0031(16) 0.0056(17)
C6 0.0432(19) 0.0499(19) 0.0416(17) 0.0005(18) 0.0027(16) -0.0013(18)
C7 0.0465(19) 0.0431(17) 0.0463(19) -0.0040(18) 0.0037(18) 0.0050(18)
C1 0.0412(17) 0.0403(18) 0.0485(19) -0.0030(17) -0.0007(16) 0.0063(17)
C12 0.0460(19) 0.057(2) 0.0482(19) -0.0001(19) 0.0047(17) 0.0038(19)
C2 0.0503(18) 0.0463(19) 0.0472(19) -0.0044(18) 0.0070(18) 0.0021(19)
C5 0.0424(17) 0.0461(19) 0.053(2) 0.0029(18) -0.0080(17) 0.0021(18)
C11 0.055(2) 0.069(2) 0.061(2) -0.011(2) -0.012(2) 0.013(2)
C8 0.059(2) 0.0487(19) 0.055(2) -0.0002(19) 0.003(2) -0.001(2)
C4 0.0537(19) 0.060(2) 0.053(2) 0.0045(19) -0.013(2) 0.004(2)
C3 0.066(2) 0.058(2) 0.0425(18) 0.0083(18) -0.0017(19) 0.004(2)
C10 0.083(3) 0.061(2) 0.052(2) 0.005(2) -0.016(2) 0.017(2)
C9 0.088(3) 0.050(2) 0.054(2) 0.008(2) 0.004(2) 0.002(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F2 C2 1.354(3) . ?
N1 C6 1.372(4) . ?
N1 C5 1.383(4) . ?
N1 C1 1.385(4) . ?
N3 C6 1.332(4) . ?
N3 N2 1.377(4) . ?
N2 C5 1.319(4) . ?
C6 C7 1.472(4) . ?
C7 C8 1.400(4) . ?
C7 C12 1.405(4) . ?
C1 C2 1.356(4) . ?
C1 H1 0.9300 . ?
C12 C11 1.390(4) . ?
C12 H12 0.9300 . ?
C2 C3 1.399(4) . ?
C5 C4 1.432(4) . ?
C11 C10 1.379(5) . ?
C11 H11 0.9300 . ?
C8 C9 1.372(5) . ?
C8 H8 0.9300 . ?
C4 C3 1.359(4) . ?
C4 H4 0.9300 . ?
C3 H3 0.9300 . ?
C10 C9 1.384(5) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?

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
C6 N1 C5 104.7(2) . . ?
C6 N1 C1 132.2(3) . . ?
C5 N1 C1 123.1(2) . . ?
C6 N3 N2 108.9(3) . . ?
C5 N2 N3 106.4(2) . . ?
N3 C6 N1 109.1(3) . . ?
N3 C6 C7 123.7(3) . . ?
N1 C6 C7 127.1(3) . . ?
C8 C7 C12 118.6(3) . . ?
C8 C7 C6 118.6(3) . . ?
C12 C7 C6 122.7(3) . . ?
C2 C1 N1 116.2(3) . . ?
C2 C1 H1 121.9 . . ?
N1 C1 H1 121.9 . . ?
C11 C12 C7 119.4(3) . . ?
C11 C12 H12 120.3 . . ?
C7 C12 H12 120.3 . . ?
F2 C2 C1 118.0(3) . . ?
F2 C2 C3 117.9(3) . . ?
C1 C2 C3 124.1(3) . . ?
N2 C5 N1 111.0(3) . . ?
N2 C5 C4 130.8(3) . . ?
N1 C5 C4 118.3(3) . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C9 C8 C7 121.1(3) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C3 C4 C5 119.3(3) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C3 C2 119.0(3) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C11 C10 C9 120.0(4) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C8 C9 C10 120.0(4) . . ?
C8 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?

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 N3 N2 C5 -0.4(4) . . . . ?
N2 N3 C6 N1 -0.1(4) . . . . ?
N2 N3 C6 C7 176.4(3) . . . . ?
C5 N1 C6 N3 0.5(4) . . . . ?
C1 N1 C6 N3 179.3(3) . . . . ?
C5 N1 C6 C7 -175.9(3) . . . . ?
C1 N1 C6 C7 2.9(6) . . . . ?
N3 C6 C7 C8 -37.7(5) . . . . ?
N1 C6 C7 C8 138.2(3) . . . . ?
N3 C6 C7 C12 140.7(4) . . . . ?
N1 C6 C7 C12 -43.4(5) . . . . ?
C6 N1 C1 C2 -178.5(3) . . . . ?
C5 N1 C1 C2 0.1(5) . . . . ?
C8 C7 C12 C11 1.0(5) . . . . ?
C6 C7 C12 C11 -177.4(3) . . . . ?
N1 C1 C2 F2 -178.7(3) . . . . ?
N1 C1 C2 C3 0.0(5) . . . . ?
N3 N2 C5 N1 0.7(4) . . . . ?
N3 N2 C5 C4 -178.5(4) . . . . ?
C6 N1 C5 N2 -0.8(4) . . . . ?
C1 N1 C5 N2 -179.7(3) . . . . ?
C6 N1 C5 C4 178.6(3) . . . . ?
C1 N1 C5 C4 -0.3(5) . . . . ?
C7 C12 C11 C10 -0.5(5) . . . . ?
C12 C7 C8 C9 -0.8(5) . . . . ?
C6 C7 C8 C9 177.7(3) . . . . ?
N2 C5 C4 C3 179.7(4) . . . . ?
N1 C5 C4 C3 0.5(5) . . . . ?
C5 C4 C3 C2 -0.4(5) . . . . ?
F2 C2 C3 C4 178.8(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C12 C11 C10 C9 -0.4(5) . . . . ?
C7 C8 C9 C10 0.0(6) . . . . ?
C11 C10 C9 C8 0.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.126
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.031
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_solvent_exptl_crystal_recrystallization_method MeOH/DCM
_chemical_compound_source        'Synthesized compound'
_chemical_properties_physical    ', Heat-sensitive'
