# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_140522b
_database_code_depnum_ccdc_archive 'CCDC 1024377'
_audit_update_record             
;
2014-09-14 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H18 F9 N9'
_chemical_formula_weight         639.50

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_H-M   P2(1)/c

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                   11.6048(14)
_cell_length_b                   11.0429(14)
_cell_length_c                   22.106(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.237(2)
_cell_angle_gamma                90.00
_cell_volume                     2825.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2033
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      20.68

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      NONE
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1296
_exptl_absorpt_coefficient_mu    0.136
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9629
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13893
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.76
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4984
_reflns_number_gt                2397
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1118P)²+1.5894P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0010(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4984
_refine_ls_number_parameters     407
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1446
_refine_ls_R_factor_gt           0.0711
_refine_ls_wR_factor_ref         0.2481
_refine_ls_wR_factor_gt          0.1935
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_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
F1 F 0.0926(2) -0.0358(3) 0.0866(2) 0.1378(15) Uani 1 1 d . . .
F2 F 0.0528(3) 0.1319(4) 0.04725(19) 0.1376(14) Uani 1 1 d . . .
F3 F 0.0743(3) 0.1189(4) 0.14054(19) 0.1512(16) Uani 1 1 d . . .
F4 F 0.7654(3) 0.2125(4) 0.2723(2) 0.1590(18) Uani 1 1 d . . .
F5 F 0.7373(4) 0.3038(8) 0.1934(2) 0.245(4) Uani 1 1 d . . .
F6 F 0.7283(3) 0.3914(4) 0.2738(3) 0.170(2) Uani 1 1 d . . .
F7 F 0.5356(3) 0.4622(3) 0.0991(3) 0.175(2) Uani 1 1 d . . .
F8 F 0.5588(3) 0.6044(4) 0.04056(18) 0.1442(15) Uani 1 1 d . . .
F9 F 0.5697(3) 0.6393(3) 0.13034(17) 0.1293(13) Uani 1 1 d . . .
N1 N 0.4235(3) 0.0945(3) 0.08201(16) 0.0600(9) Uani 1 1 d . . .
N2 N 0.3935(4) 0.2130(3) 0.0840(2) 0.0844(12) Uani 1 1 d . . .
N3 N 0.2823(3) 0.2177(3) 0.0880(2) 0.0846(13) Uani 1 1 d . . .
N4 N 0.3936(3) 0.2674(3) 0.24888(15) 0.0598(9) Uani 1 1 d . . .
N5 N 0.4230(3) 0.1541(3) 0.23276(18) 0.0739(11) Uani 1 1 d . . .
N6 N 0.5357(3) 0.1538(3) 0.22955(18) 0.0760(11) Uani 1 1 d . . .
N7 N 0.2014(3) 0.5905(3) 0.08394(16) 0.0611(9) Uani 1 1 d . . .
N8 N 0.2329(4) 0.7078(3) 0.0797(2) 0.0884(13) Uani 1 1 d . . .
N9 N 0.3455(4) 0.7121(3) 0.0816(2) 0.0876(13) Uani 1 1 d . . .
C1 C 0.1172(4) 0.0790(4) 0.0910(3) 0.0768(13) Uani 1 1 d . . .
C2 C 0.2412(4) 0.1031(4) 0.08855(19) 0.0599(11) Uani 1 1 d . . .
C3 C 0.3297(3) 0.0248(4) 0.08459(19) 0.0607(11) Uani 1 1 d . . .
H3 H 0.3262 -0.0593 0.0838 0.073 Uiso 1 1 calc R . .
C4 C 0.5421(3) 0.0609(4) 0.07769(18) 0.0601(11) Uani 1 1 d . . .
C5 C 0.6227(4) 0.1473(4) 0.0655(2) 0.0837(15) Uani 1 1 d . . .
H5 H 0.6006 0.2276 0.0596 0.100 Uiso 1 1 calc R . .
C6 C 0.7361(5) 0.1137(6) 0.0622(3) 0.0993(18) Uani 1 1 d . . .
H6 H 0.7910 0.1721 0.0547 0.119 Uiso 1 1 calc R . .
C7 C 0.7689(4) -0.0048(6) 0.0698(2) 0.0867(15) Uani 1 1 d . . .
H7 H 0.8458 -0.0269 0.0672 0.104 Uiso 1 1 calc R . .
C8 C 0.6882(4) -0.0908(5) 0.0812(2) 0.0858(15) Uani 1 1 d . . .
H8 H 0.7106 -0.1712 0.0866 0.103 Uiso 1 1 calc R . .
C9 C 0.5742(4) -0.0589(4) 0.0847(2) 0.0754(13) Uani 1 1 d . . .
H9 H 0.5193 -0.1176 0.0917 0.090 Uiso 1 1 calc R . .
C10 C 0.6987(4) 0.2939(5) 0.2445(3) 0.0889(16) Uani 1 1 d . . .
C11 C 0.5759(4) 0.2665(4) 0.2436(2) 0.0662(12) Uani 1 1 d . . .
C12 C 0.4867(3) 0.3390(4) 0.2560(2) 0.0646(12) Uani 1 1 d . . .
H12 H 0.4894 0.4203 0.2669 0.077 Uiso 1 1 calc R . .
C13 C 0.2765(3) 0.2950(4) 0.25936(19) 0.0617(11) Uani 1 1 d . . .
C14 C 0.2024(4) 0.2024(5) 0.2726(2) 0.0855(15) Uani 1 1 d . . .
H14 H 0.2273 0.1224 0.2733 0.103 Uiso 1 1 calc R . .
C15 C 0.0904(5) 0.2311(6) 0.2848(3) 0.1022(18) Uani 1 1 d . . .
H15 H 0.0398 0.1695 0.2938 0.123 Uiso 1 1 calc R . .
C16 C 0.0531(4) 0.3487(6) 0.2839(3) 0.0981(18) Uani 1 1 d . . .
H16 H -0.0230 0.3665 0.2912 0.118 Uiso 1 1 calc R . .
C17 C 0.1277(4) 0.4396(5) 0.2721(3) 0.0945(17) Uani 1 1 d . . .
H17 H 0.1029 0.5196 0.2728 0.113 Uiso 1 1 calc R . .
C18 C 0.2400(4) 0.4138(5) 0.2591(2) 0.0810(14) Uani 1 1 d . . .
H18 H 0.2902 0.4759 0.2502 0.097 Uiso 1 1 calc R . .
C19 C 0.5106(4) 0.5729(5) 0.0909(3) 0.0761(13) Uani 1 1 d . . .
C20 C 0.3857(4) 0.5971(4) 0.0874(2) 0.0620(11) Uani 1 1 d . . .
C21 C 0.2962(3) 0.5199(4) 0.0890(2) 0.0646(12) Uani 1 1 d . . .
H21 H 0.2992 0.4361 0.0929 0.077 Uiso 1 1 calc R . .
C22 C 0.0820(4) 0.5584(4) 0.08334(19) 0.0630(11) Uani 1 1 d . . .
C23 C 0.0520(4) 0.4524(4) 0.1103(2) 0.0766(13) Uani 1 1 d . . .
H23 H 0.1085 0.4031 0.1295 0.092 Uiso 1 1 calc R . .
C24 C -0.0633(4) 0.4197(5) 0.1087(3) 0.0935(16) Uani 1 1 d . . .
H24 H -0.0844 0.3475 0.1265 0.112 Uiso 1 1 calc R . .
C25 C -0.1457(5) 0.4924(6) 0.0813(3) 0.0994(18) Uani 1 1 d . . .
H25 H -0.2230 0.4702 0.0808 0.119 Uiso 1 1 calc R . .
C26 C -0.1158(5) 0.5980(6) 0.0544(3) 0.0972(17) Uani 1 1 d . . .
H26 H -0.1729 0.6472 0.0357 0.117 Uiso 1 1 calc R . .
C27 C -0.0005(4) 0.6324(4) 0.0548(2) 0.0796(14) Uani 1 1 d . . .
H27 H 0.0204 0.7039 0.0363 0.095 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C1 1.302(5) . ?
F2 C1 1.314(6) . ?
F3 C1 1.313(6) . ?
F4 C10 1.309(6) . ?
F5 C10 1.251(6) . ?
F6 C10 1.290(6) . ?
F7 C19 1.266(5) . ?
F8 C19 1.329(6) . ?
F9 C19 1.296(5) . ?
N1 C3 1.338(5) . ?
N1 N2 1.356(5) . ?
N1 C4 1.435(5) . ?
N2 N3 1.301(5) . ?
N3 C2 1.354(5) . ?
N4 C12 1.339(5) . ?
N4 N5 1.351(4) . ?
N4 C13 1.428(5) . ?
N5 N6 1.315(5) . ?
N6 C11 1.357(5) . ?
N7 C21 1.347(5) . ?
N7 N8 1.351(5) . ?
N7 C22 1.429(5) . ?
N8 N9 1.305(5) . ?
N9 C20 1.356(5) . ?
C1 C2 1.468(6) . ?
C2 C3 1.350(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(6) . ?
C4 C9 1.380(6) . ?
C5 C6 1.374(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.370(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.377(6) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C10 C11 1.456(6) . ?
C11 C12 1.352(6) . ?
C12 H12 0.9300 . ?
C13 C18 1.379(6) . ?
C13 C14 1.380(6) . ?
C14 C15 1.384(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.369(7) . ?
C15 H15 0.9300 . ?
C16 C17 1.363(7) . ?
C16 H16 0.9300 . ?
C17 C18 1.385(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.470(6) . ?
C20 C21 1.346(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.370(6) . ?
C22 C27 1.376(6) . ?
C23 C24 1.385(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.357(7) . ?
C24 H24 0.9300 . ?
C25 C26 1.365(8) . ?
C25 H25 0.9300 . ?
C26 C27 1.390(7) . ?
C26 H26 0.9300 . ?
C27 H27 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
C3 N1 N2 110.0(3) . . ?
C3 N1 C4 129.9(3) . . ?
N2 N1 C4 120.1(3) . . ?
N3 N2 N1 107.4(3) . . ?
N2 N3 C2 108.4(3) . . ?
C12 N4 N5 111.1(3) . . ?
C12 N4 C13 128.6(4) . . ?
N5 N4 C13 120.1(3) . . ?
N6 N5 N4 106.8(3) . . ?
N5 N6 C11 108.1(3) . . ?
C21 N7 N8 109.7(3) . . ?
C21 N7 C22 130.0(3) . . ?
N8 N7 C22 120.3(3) . . ?
N9 N8 N7 108.0(3) . . ?
N8 N9 C20 107.8(4) . . ?
F1 C1 F2 105.6(5) . . ?
F1 C1 F3 107.1(5) . . ?
F2 C1 F3 103.6(4) . . ?
F1 C1 C2 112.5(4) . . ?
F2 C1 C2 113.5(4) . . ?
F3 C1 C2 113.7(4) . . ?
C3 C2 N3 109.1(4) . . ?
C3 C2 C1 129.7(4) . . ?
N3 C2 C1 121.1(4) . . ?
N1 C3 C2 105.1(3) . . ?
N1 C3 H3 127.5 . . ?
C2 C3 H3 127.5 . . ?
C5 C4 C9 120.3(4) . . ?
C5 C4 N1 120.1(4) . . ?
C9 C4 N1 119.5(4) . . ?
C6 C5 C4 119.4(5) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C7 C6 C5 120.7(5) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 C6 119.8(5) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 H7 120.1 . . ?
C7 C8 C9 120.4(5) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C8 C9 C4 119.4(4) . . ?
C8 C9 H9 120.3 . . ?
C4 C9 H9 120.3 . . ?
F5 C10 F6 106.3(6) . . ?
F5 C10 F4 104.2(5) . . ?
F6 C10 F4 102.2(5) . . ?
F5 C10 C11 114.9(6) . . ?
F6 C10 C11 113.9(5) . . ?
F4 C10 C11 114.1(5) . . ?
C12 C11 N6 109.5(4) . . ?
C12 C11 C10 129.6(4) . . ?
N6 C11 C10 120.9(4) . . ?
N4 C12 C11 104.5(4) . . ?
N4 C12 H12 127.8 . . ?
C11 C12 H12 127.8 . . ?
C18 C13 C14 120.6(4) . . ?
C18 C13 N4 119.9(4) . . ?
C14 C13 N4 119.4(4) . . ?
C13 C14 C15 118.7(5) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C16 C15 C14 121.0(5) . . ?
C16 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C17 C16 C15 119.8(5) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.6(5) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C13 C18 C17 119.2(5) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
F7 C19 F9 110.2(5) . . ?
F7 C19 F8 105.5(5) . . ?
F9 C19 F8 100.4(4) . . ?
F7 C19 C20 113.4(4) . . ?
F9 C19 C20 113.8(4) . . ?
F8 C19 C20 112.5(4) . . ?
C21 C20 N9 109.6(4) . . ?
C21 C20 C19 130.0(4) . . ?
N9 C20 C19 120.4(4) . . ?
C20 C21 N7 105.0(4) . . ?
C20 C21 H21 127.5 . . ?
N7 C21 H21 127.5 . . ?
C23 C22 C27 121.1(4) . . ?
C23 C22 N7 119.0(4) . . ?
C27 C22 N7 119.9(4) . . ?
C22 C23 C24 119.2(5) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 120.3(5) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.5(5) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C25 C26 C27 120.3(5) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C22 C27 C26 118.5(5) . . ?
C22 C27 H27 120.7 . . ?
C26 C27 H27 120.7 . . ?

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
C3 N1 N2 N3 0.1(5) . . . . ?
C4 N1 N2 N3 -179.9(4) . . . . ?
N1 N2 N3 C2 0.0(5) . . . . ?
C12 N4 N5 N6 0.0(5) . . . . ?
C13 N4 N5 N6 -176.6(3) . . . . ?
N4 N5 N6 C11 0.0(5) . . . . ?
C21 N7 N8 N9 0.5(5) . . . . ?
C22 N7 N8 N9 179.8(4) . . . . ?
N7 N8 N9 C20 -0.4(6) . . . . ?
N2 N3 C2 C3 -0.2(6) . . . . ?
N2 N3 C2 C1 -178.2(4) . . . . ?
F1 C1 C2 C3 -2.4(8) . . . . ?
F2 C1 C2 C3 -122.2(5) . . . . ?
F3 C1 C2 C3 119.7(5) . . . . ?
F1 C1 C2 N3 175.2(5) . . . . ?
F2 C1 C2 N3 55.3(7) . . . . ?
F3 C1 C2 N3 -62.8(6) . . . . ?
N2 N1 C3 C2 -0.3(5) . . . . ?
C4 N1 C3 C2 179.7(4) . . . . ?
N3 C2 C3 N1 0.3(5) . . . . ?
C1 C2 C3 N1 178.1(5) . . . . ?
C3 N1 C4 C5 169.2(4) . . . . ?
N2 N1 C4 C5 -10.8(6) . . . . ?
C3 N1 C4 C9 -9.6(7) . . . . ?
N2 N1 C4 C9 170.4(4) . . . . ?
C9 C4 C5 C6 -1.9(7) . . . . ?
N1 C4 C5 C6 179.3(4) . . . . ?
C4 C5 C6 C7 1.2(8) . . . . ?
C5 C6 C7 C8 -0.5(9) . . . . ?
C6 C7 C8 C9 0.5(8) . . . . ?
C7 C8 C9 C4 -1.2(8) . . . . ?
C5 C4 C9 C8 1.9(7) . . . . ?
N1 C4 C9 C8 -179.3(4) . . . . ?
N5 N6 C11 C12 0.1(5) . . . . ?
N5 N6 C11 C10 179.3(5) . . . . ?
F5 C10 C11 C12 -106.0(7) . . . . ?
F6 C10 C11 C12 16.8(9) . . . . ?
F4 C10 C11 C12 133.7(6) . . . . ?
F5 C10 C11 N6 74.9(7) . . . . ?
F6 C10 C11 N6 -162.2(5) . . . . ?
F4 C10 C11 N6 -45.3(8) . . . . ?
N5 N4 C12 C11 0.1(5) . . . . ?
C13 N4 C12 C11 176.3(4) . . . . ?
N6 C11 C12 N4 -0.1(5) . . . . ?
C10 C11 C12 N4 -179.2(5) . . . . ?
C12 N4 C13 C18 22.1(7) . . . . ?
N5 N4 C13 C18 -162.0(4) . . . . ?
C12 N4 C13 C14 -154.8(4) . . . . ?
N5 N4 C13 C14 21.1(6) . . . . ?
C18 C13 C14 C15 0.8(7) . . . . ?
N4 C13 C14 C15 177.7(4) . . . . ?
C13 C14 C15 C16 0.0(8) . . . . ?
C14 C15 C16 C17 -1.5(9) . . . . ?
C15 C16 C17 C18 2.2(9) . . . . ?
C14 C13 C18 C17 -0.2(7) . . . . ?
N4 C13 C18 C17 -177.0(4) . . . . ?
C16 C17 C18 C13 -1.3(8) . . . . ?
N8 N9 C20 C21 0.1(6) . . . . ?
N8 N9 C20 C19 -179.8(4) . . . . ?
F7 C19 C20 C21 -3.0(8) . . . . ?
F9 C19 C20 C21 -130.1(5) . . . . ?
F8 C19 C20 C21 116.6(6) . . . . ?
F7 C19 C20 N9 176.8(5) . . . . ?
F9 C19 C20 N9 49.7(7) . . . . ?
F8 C19 C20 N9 -63.6(6) . . . . ?
N9 C20 C21 N7 0.2(5) . . . . ?
C19 C20 C21 N7 -179.9(5) . . . . ?
N8 N7 C21 C20 -0.5(5) . . . . ?
C22 N7 C21 C20 -179.6(4) . . . . ?
C21 N7 C22 C23 24.3(7) . . . . ?
N8 N7 C22 C23 -154.8(4) . . . . ?
C21 N7 C22 C27 -154.4(5) . . . . ?
N8 N7 C22 C27 26.6(6) . . . . ?
C27 C22 C23 C24 0.0(7) . . . . ?
N7 C22 C23 C24 -178.6(4) . . . . ?
C22 C23 C24 C25 -0.7(8) . . . . ?
C23 C24 C25 C26 0.7(9) . . . . ?
C24 C25 C26 C27 -0.1(9) . . . . ?
C23 C22 C27 C26 0.6(7) . . . . ?
N7 C22 C27 C26 179.2(4) . . . . ?
C25 C26 C27 C22 -0.6(8) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.374
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.056
####################################################################### 
# 
# 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_140107a
_database_code_depnum_ccdc_archive 'CCDC 1024379'
_audit_update_record             
;
2014-09-14 deposited with the CCDC.
2015-09-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H7 F6 N3'
_chemical_formula_weight         295.20

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_H-M   P2(1)/c

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                   10.630(7)
_cell_length_b                   8.222(5)
_cell_length_c                   13.645(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.814(5)
_cell_angle_gamma                90.00
_cell_volume                     1171.5(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2571
_cell_measurement_theta_min      3.0
_cell_measurement_theta_max      27.5

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             592
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9539
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      294(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  'Rigaku Mercury375R'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 13.6612
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11814
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_sigmaI/netI    0.0283
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.46
_reflns_number_total             2680
_reflns_number_gt                2127
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.0799P)²+0.2848P] 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         2680
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0517
_refine_ls_wR_factor_ref         0.1525
_refine_ls_wR_factor_gt          0.1428
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
C1 C 0.64269(19) 0.0257(3) 0.90252(15) 0.0611(5) Uani 1 1 d . . .
C2 C 0.76951(16) 0.0561(2) 0.87431(13) 0.0455(4) Uani 1 1 d . . .
C3 C 0.81469(15) 0.0100(2) 0.79096(12) 0.0394(4) Uani 1 1 d . . .
C4 C 0.76056(16) -0.0925(2) 0.70281(13) 0.0450(4) Uani 1 1 d . . .
H4A H 0.7219 -0.1886 0.7259 0.054 Uiso 1 1 calc R . .
H4B H 0.8301 -0.1284 0.6711 0.054 Uiso 1 1 calc R . .
C5 C 0.66199(18) -0.0078(3) 0.62623(14) 0.0532(5) Uani 1 1 d . . .
C6 C 1.03558(15) 0.05367(19) 0.75050(13) 0.0402(4) Uani 1 1 d . . .
C7 C 1.02188(17) 0.1125(2) 0.65432(14) 0.0477(4) Uani 1 1 d . . .
H7 H 0.9462 0.1626 0.6238 0.057 Uiso 1 1 calc R . .
C8 C 1.12323(19) 0.0954(3) 0.60401(15) 0.0553(5) Uani 1 1 d . . .
H8 H 1.1159 0.1346 0.5392 0.066 Uiso 1 1 calc R . .
C9 C 1.23509(19) 0.0202(3) 0.65016(16) 0.0575(5) Uani 1 1 d . . .
H9 H 1.3025 0.0084 0.6160 0.069 Uiso 1 1 calc R . .
C10 C 1.24743(17) -0.0374(3) 0.74628(16) 0.0546(5) Uani 1 1 d . . .
H10 H 1.3232 -0.0872 0.7768 0.065 Uiso 1 1 calc R . .
C11 C 1.14742(16) -0.0214(2) 0.79761(14) 0.0462(4) Uani 1 1 d . . .
H11 H 1.1551 -0.0604 0.8624 0.055 Uiso 1 1 calc R . .
F1 F 0.58648(13) -0.1069(2) 0.85868(12) 0.0835(5) Uani 1 1 d . . .
F2 F 0.55957(14) 0.1445(2) 0.87367(16) 0.1072(6) Uani 1 1 d . . .
F3 F 0.65106(16) 0.0094(3) 0.99872(11) 0.1247(9) Uani 1 1 d . . .
F4 F 0.56196(13) 0.0424(2) 0.66264(11) 0.0907(5) Uani 1 1 d . . .
F5 F 0.70823(13) 0.12217(17) 0.58734(11) 0.0798(4) Uani 1 1 d . . .
F6 F 0.61803(14) -0.1068(2) 0.55071(10) 0.0835(5) Uani 1 1 d . . .
N1 N 0.86015(15) 0.1427(2) 0.93605(12) 0.0530(4) Uani 1 1 d . . .
N2 N 0.96146(14) 0.1532(2) 0.89530(11) 0.0516(4) Uani 1 1 d . . .
N3 N 0.93490(13) 0.07331(17) 0.80687(10) 0.0411(3) Uani 1 1 d . . .


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

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
C1 F3 1.306(3) . ?
C1 F2 1.326(3) . ?
C1 F1 1.330(3) . ?
C1 C2 1.491(3) . ?
C2 N1 1.356(2) . ?
C2 C3 1.369(3) . ?
C3 N3 1.359(2) . ?
C3 C4 1.493(2) . ?
C4 C5 1.505(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 F4 1.321(2) . ?
C5 F6 1.327(2) . ?
C5 F5 1.328(2) . ?
C6 C7 1.380(3) . ?
C6 C11 1.386(2) . ?
C6 N3 1.440(2) . ?
C7 C8 1.389(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.383(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.385(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
N1 N2 1.304(2) . ?
N2 N3 1.356(2) . ?

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
F3 C1 F2 106.9(2) . . ?
F3 C1 F1 107.9(2) . . ?
F2 C1 F1 104.61(17) . . ?
F3 C1 C2 112.48(17) . . ?
F2 C1 C2 112.59(19) . . ?
F1 C1 C2 111.90(18) . . ?
N1 C2 C3 110.03(16) . . ?
N1 C2 C1 119.93(17) . . ?
C3 C2 C1 130.04(17) . . ?
N3 C3 C2 103.12(15) . . ?
N3 C3 C4 123.63(15) . . ?
C2 C3 C4 133.15(16) . . ?
C3 C4 C5 114.28(15) . . ?
C3 C4 H4A 108.7 . . ?
C5 C4 H4A 108.7 . . ?
C3 C4 H4B 108.7 . . ?
C5 C4 H4B 108.7 . . ?
H4A C4 H4B 107.6 . . ?
F4 C5 F6 107.01(16) . . ?
F4 C5 F5 106.45(19) . . ?
F6 C5 F5 106.62(17) . . ?
F4 C5 C4 112.84(16) . . ?
F6 C5 C4 110.69(18) . . ?
F5 C5 C4 112.85(16) . . ?
C7 C6 C11 121.69(16) . . ?
C7 C6 N3 120.82(15) . . ?
C11 C6 N3 117.46(16) . . ?
C6 C7 C8 118.76(17) . . ?
C6 C7 H7 120.6 . . ?
C8 C7 H7 120.6 . . ?
C9 C8 C7 120.04(19) . . ?
C9 C8 H8 120.0 . . ?
C7 C8 H8 120.0 . . ?
C10 C9 C8 120.50(18) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.27(18) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C6 118.73(18) . . ?
C10 C11 H11 120.6 . . ?
C6 C11 H11 120.6 . . ?
N2 N1 C2 108.48(15) . . ?
N1 N2 N3 107.25(14) . . ?
N2 N3 C3 111.12(14) . . ?
N2 N3 C6 118.57(13) . . ?
C3 N3 C6 129.99(14) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
F3 C1 C2 N1 -33.5(3) . . . . ?
F2 C1 C2 N1 87.3(2) . . . . ?
F1 C1 C2 N1 -155.22(18) . . . . ?
F3 C1 C2 C3 146.9(2) . . . . ?
F2 C1 C2 C3 -92.3(3) . . . . ?
F1 C1 C2 C3 25.2(3) . . . . ?
N1 C2 C3 N3 -0.04(19) . . . . ?
C1 C2 C3 N3 179.59(19) . . . . ?
N1 C2 C3 C4 176.10(17) . . . . ?
C1 C2 C3 C4 -4.3(3) . . . . ?
N3 C3 C4 C5 -106.64(19) . . . . ?
C2 C3 C4 C5 77.9(2) . . . . ?
C3 C4 C5 F4 -59.8(2) . . . . ?
C3 C4 C5 F6 -179.64(15) . . . . ?
C3 C4 C5 F5 61.0(2) . . . . ?
C11 C6 C7 C8 0.0(3) . . . . ?
N3 C6 C7 C8 177.90(16) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C6 -0.2(3) . . . . ?
C7 C6 C11 C10 0.0(3) . . . . ?
N3 C6 C11 C10 -177.98(16) . . . . ?
C3 C2 N1 N2 -0.1(2) . . . . ?
C1 C2 N1 N2 -179.81(17) . . . . ?
C2 N1 N2 N3 0.3(2) . . . . ?
N1 N2 N3 C3 -0.3(2) . . . . ?
N1 N2 N3 C6 -174.41(15) . . . . ?
C2 C3 N3 N2 0.20(18) . . . . ?
C4 C3 N3 N2 -176.42(15) . . . . ?
C2 C3 N3 C6 173.45(16) . . . . ?
C4 C3 N3 C6 -3.2(3) . . . . ?
C7 C6 N3 N2 -121.90(18) . . . . ?
C11 C6 N3 N2 56.1(2) . . . . ?
C7 C6 N3 C3 65.3(2) . . . . ?
C11 C6 N3 C3 -116.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.044


