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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_DB32
_database_code_depnum_ccdc_archive 'CCDC 982084'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 F2 N2'
_chemical_formula_sum            'C13 H10 F2 N2'
_chemical_formula_weight         232.23

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.229(3)
_cell_length_b                   10.526(4)
_cell_length_c                   12.346(4)
_cell_angle_alpha                66.680(10)
_cell_angle_beta                 78.973(11)
_cell_angle_gamma                67.688(10)
_cell_volume                     1128.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    23742
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      27.67

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_F_000             480
_exptl_transmission_factor_min   0.694
_exptl_transmission_factor_max   0.768
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.106
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26511
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0599
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.530
_diffrn_reflns_theta_max         27.877
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5317
_reflns_number_gt                3759
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0492P)²+0.4074P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5317
_refine_ls_number_parameters     331
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F4A F 1.0166(2) 1.0296(2) 0.11090(19) 0.0528(4) Uani 0.5389(19) 1 d . . P A 1
C20A C 1.04131(15) 0.77038(18) 0.40705(15) 0.0291(4) Uani 0.5389(19) 1 d . . P
A 1
C21A C 1.07252(18) 0.6451(2) 0.37932(16) 0.0350(4) Uani 0.5389(19) 1 d . . P A
1
H21A H 1.0859 0.5518 0.4403 0.042 Uiso 0.5389(19) 1 calc R U P A 1
C22A C 1.0837(2) 0.6584(2) 0.26270(19) 0.0460(5) Uani 0.5389(19) 1 d . . P A 1
H22A H 1.1056 0.5724 0.2449 0.055 Uiso 0.5389(19) 1 calc R U P A 1
C23A C 1.0645(2) 0.7908(3) 0.17084(19) 0.0493(5) Uani 0.5389(19) 1 d . . P A 1
H23A H 1.0713 0.7980 0.0909 0.059 Uiso 0.5389(19) 1 calc R U P A 1
C24A C 1.03499(19) 0.9118(2) 0.20028(18) 0.0471(5) Uani 0.5389(19) 1 d . . P A
1
C25A C 1.02372(16) 0.90610(19) 0.31491(17) 0.0361(4) Uani 0.5389(19) 1 d . . P
A 1
H25A H 1.0044 0.9926 0.3313 0.043 Uiso 0.5389(19) 1 calc R U P A 1
F4B F 1.1201(3) 0.5539(3) 0.2258(2) 0.0528(4) Uani 0.4611(19) 1 d . . P A 2
C20B C 1.04131(15) 0.77038(18) 0.40705(15) 0.0291(4) Uani 0.4611(19) 1 d . . P
A 2
C21B C 1.02372(16) 0.90610(19) 0.31491(17) 0.0361(4) Uani 0.4611(19) 1 d . . P
A 2
H21B H 1.0044 0.9926 0.3313 0.043 Uiso 0.4611(19) 1 calc R U P A 2
C22B C 1.03499(19) 0.9118(2) 0.20028(18) 0.0471(5) Uani 0.4611(19) 1 d . . P A
2
H22B H 1.0216 1.0044 0.1384 0.056 Uiso 0.4611(19) 1 calc R U P A 2
C23B C 1.0645(2) 0.7908(3) 0.17084(19) 0.0493(5) Uani 0.4611(19) 1 d . . P A 2
H23B H 1.0713 0.7980 0.0909 0.059 Uiso 0.4611(19) 1 calc R U P A 2
C24B C 1.0837(2) 0.6584(2) 0.26270(19) 0.0460(5) Uani 0.4611(19) 1 d . . P A 2
C25B C 1.07252(18) 0.6451(2) 0.37932(16) 0.0350(4) Uani 0.4611(19) 1 d . . P A
2
H25B H 1.0859 0.5518 0.4403 0.042 Uiso 0.4611(19) 1 calc R U P A 2
F2A F 0.36234(15) 0.66363(13) 1.04710(10) 0.0546(4) Uani 0.952(2) 1 d . . P B 1
C7A C 0.43805(15) 0.82641(18) 0.73433(14) 0.0264(3) Uani 0.952(2) 1 d . . P B 1
C8A C 0.42597(18) 0.72144(18) 0.84483(15) 0.0321(4) Uani 0.952(2) 1 d . . P B 1
H8A H 0.4531 0.6208 0.8544 0.038 Uiso 0.952(2) 1 calc R U P B 1
C9A C 0.3738(2) 0.7668(2) 0.93974(16) 0.0367(4) Uani 0.952(2) 1 d . . P B 1
C10A C 0.33205(19) 0.9110(2) 0.93178(17) 0.0366(4) Uani 0.952(2) 1 d . . P B 1
H10A H 0.2956 0.9385 0.9991 0.044 Uiso 0.952(2) 1 calc R U P B 1
C11A C 0.34537(18) 1.0142(2) 0.82167(17) 0.0362(4) Uani 0.952(2) 1 d . . P B 1
H11A H 0.3178 1.1145 0.8131 0.043 Uiso 0.952(2) 1 calc R U P B 1
C12A C 0.39828(16) 0.97350(18) 0.72355(16) 0.0308(4) Uani 0.952(2) 1 d . . P B
1
H12A H 0.4075 1.0457 0.6489 0.037 Uiso 0.952(2) 1 calc R U P B 1
F2B F 0.303(3) 1.138(3) 0.813(2) 0.0546(4) Uani 0.048(2) 1 d . . P B 2
C7B C 0.43805(15) 0.82641(18) 0.73433(14) 0.0264(3) Uani 0.048(2) 1 d . . P B 2
C8B C 0.39828(16) 0.97350(18) 0.72355(16) 0.0308(4) Uani 0.048(2) 1 d . . P B 2
H8B H 0.4075 1.0457 0.6489 0.037 Uiso 0.048(2) 1 calc R U P B 2
C9B C 0.34537(18) 1.0142(2) 0.82167(17) 0.0362(4) Uani 0.048(2) 1 d . . P B 2
C10B C 0.33205(19) 0.9110(2) 0.93178(17) 0.0366(4) Uani 0.048(2) 1 d . . P B 2
H10B H 0.2956 0.9385 0.9991 0.044 Uiso 0.048(2) 1 calc R U P B 2
C11B C 0.3738(2) 0.7668(2) 0.93974(16) 0.0367(4) Uani 0.048(2) 1 d . . P B 2
H11B H 0.3662 0.6947 1.0149 0.044 Uiso 0.048(2) 1 calc R U P B 2
C12B C 0.42597(18) 0.72144(18) 0.84483(15) 0.0321(4) Uani 0.048(2) 1 d . . P B
2
H12B H 0.4531 0.6208 0.8544 0.038 Uiso 0.048(2) 1 calc R U P B 2
F1 F 0.63006(11) 0.56544(12) 0.20347(9) 0.0438(3) Uani 1 1 d . . . . .
N2 N 0.26693(15) 0.82320(17) 0.59377(15) 0.0338(4) Uani 1 1 d . . . . .
H2A H 0.232(2) 0.852(2) 0.6541(17) 0.036(5) Uiso 1 1 d . . . . .
H2B H 0.214(2) 0.797(2) 0.5653(17) 0.040(5) Uiso 1 1 d . . . . .
C13 C 0.40904(15) 0.77873(16) 0.57433(14) 0.0244(3) Uani 1 1 d . . . . .
N1 N 0.49696(13) 0.78271(15) 0.63514(12) 0.0268(3) Uani 1 1 d . . . . .
C4 C 0.57583(17) 0.61887(19) 0.29276(15) 0.0301(4) Uani 1 1 d . . . . .
C3 C 0.44224(17) 0.72206(19) 0.28433(15) 0.0317(4) Uani 1 1 d . . . . .
H3 H 0.3887 0.7560 0.2173 0.038 Uiso 1 1 calc R U . . .
C2 C 0.38770(16) 0.77529(17) 0.37553(14) 0.0276(4) Uani 1 1 d . . . . .
H2 H 0.2959 0.8470 0.3709 0.033 Uiso 1 1 calc R U . . .
C1 C 0.46625(15) 0.72468(16) 0.47456(14) 0.0233(3) Uani 1 1 d . . . . .
C6 C 0.60119(15) 0.61873(16) 0.47972(14) 0.0247(3) Uani 1 1 d . . . . .
H6 H 0.6551 0.5826 0.5469 0.030 Uiso 1 1 calc R U . . .
C5 C 0.65718(16) 0.56604(18) 0.38856(15) 0.0290(4) Uani 1 1 d . . . . .
H5 H 0.7493 0.4953 0.3917 0.035 Uiso 1 1 calc R U . . .
F3 F 0.85969(13) 0.71476(15) 1.05887(11) 0.0573(3) Uani 1 1 d . . . . .
N3 N 1.03418(13) 0.76035(15) 0.52629(13) 0.0300(3) Uani 1 1 d . . . . .
N4 N 0.79644(16) 0.77891(17) 0.53846(16) 0.0351(4) Uani 1 1 d . . . . .
H4B H 0.719(2) 0.777(2) 0.5818(19) 0.049(6) Uiso 1 1 d . . . . .
H4A H 0.803(2) 0.793(2) 0.461(2) 0.047(6) Uiso 1 1 d . . . . .
C26 C 0.91333(15) 0.76438(16) 0.58466(15) 0.0267(4) Uani 1 1 d . . . . .
C14 C 0.89954(16) 0.75241(17) 0.71019(16) 0.0281(4) Uani 1 1 d . . . . .
C19 C 1.01656(17) 0.67605(18) 0.78080(15) 0.0305(4) Uani 1 1 d . . . . .
H19 H 1.1060 0.6318 0.7480 0.037 Uiso 1 1 calc R U . . .
C18 C 1.00404(19) 0.66389(19) 0.89770(16) 0.0363(4) Uani 1 1 d . . . . .
H18 H 1.0839 0.6126 0.9453 0.044 Uiso 1 1 calc R U . . .
C17 C 0.8730(2) 0.7279(2) 0.94341(17) 0.0400(4) Uani 1 1 d . . . . .
C15 C 0.76961(17) 0.8177(2) 0.76012(18) 0.0367(4) Uani 1 1 d . . . . .
H15 H 0.6895 0.8716 0.7128 0.044 Uiso 1 1 calc R U . . .
C16 C 0.75535(19) 0.8055(2) 0.87703(19) 0.0441(5) Uani 1 1 d . . . . .
H16 H 0.6665 0.8496 0.9107 0.053 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F4A C24A 1.269(3) . ?
C20A C21A 1.397(2) . ?
C20A C25A 1.401(2) . ?
C20A N3 1.423(2) . ?
C21A C22A 1.377(3) . ?
C21A H21A 0.9500 . ?
C22A C23A 1.376(3) . ?
C22A H22A 0.9500 . ?
C23A C24A 1.370(3) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.377(3) . ?
C25A H25A 0.9500 . ?
F4B C24B 1.255(3) . ?
C20B C25B 1.397(2) . ?
C20B C21B 1.401(2) . ?
C20B N3 1.423(2) . ?
C21B C22B 1.377(3) . ?
C21B H21B 0.9500 . ?
C22B C23B 1.370(3) . ?
C22B H22B 0.9500 . ?
C23B C24B 1.376(3) . ?
C23B H23B 0.9500 . ?
C24B C25B 1.377(3) . ?
C25B H25B 0.9500 . ?
F2A C9A 1.359(2) . ?
C7A C8A 1.394(2) . ?
C7A C12A 1.400(2) . ?
C7A N1 1.424(2) . ?
C8A C9A 1.377(2) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.379(3) . ?
C10A C11A 1.385(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.388(3) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
F2B C9B 1.18(2) . ?
C7B C12B 1.394(2) . ?
C7B C8B 1.400(2) . ?
C7B N1 1.424(2) . ?
C8B C9B 1.388(3) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.385(3) . ?
C10B C11B 1.379(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.377(2) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
F1 C4 1.3636(19) . ?
N2 C13 1.352(2) . ?
N2 H2A 0.88(2) . ?
N2 H2B 0.87(2) . ?
C13 N1 1.298(2) . ?
C13 C1 1.486(2) . ?
C4 C3 1.377(2) . ?
C4 C5 1.380(2) . ?
C3 C2 1.384(2) . ?
C3 H3 0.9500 . ?
C2 C1 1.400(2) . ?
C2 H2 0.9500 . ?
C1 C6 1.401(2) . ?
C6 C5 1.382(2) . ?
C6 H6 0.9500 . ?
C5 H5 0.9500 . ?
F3 C17 1.362(2) . ?
N3 C26 1.301(2) . ?
N4 C26 1.353(2) . ?
N4 H4B 0.86(2) . ?
N4 H4A 0.91(2) . ?
C26 C14 1.488(2) . ?
C14 C15 1.395(2) . ?
C14 C19 1.397(2) . ?
C19 C18 1.382(3) . ?
C19 H19 0.9500 . ?
C18 C17 1.377(3) . ?
C18 H18 0.9500 . ?
C17 C16 1.374(3) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21A C20A C25A 118.87(17) . . ?
C21A C20A N3 120.98(15) . . ?
C25A C20A N3 120.08(16) . . ?
C22A C21A C20A 119.33(18) . . ?
C22A C21A H21A 120.3 . . ?
C20A C21A H21A 120.3 . . ?
C23A C22A C21A 122.81(19) . . ?
C23A C22A H22A 118.6 . . ?
C21A C22A H22A 118.6 . . ?
C24A C23A C22A 116.74(19) . . ?
C24A C23A H23A 121.6 . . ?
C22A C23A H23A 121.6 . . ?
F4A C24A C23A 112.8(2) . . ?
F4A C24A C25A 123.7(2) . . ?
C23A C24A C25A 123.42(19) . . ?
C24A C25A C20A 118.81(18) . . ?
C24A C25A H25A 120.6 . . ?
C20A C25A H25A 120.6 . . ?
C25B C20B C21B 118.87(17) . . ?
C25B C20B N3 120.98(15) . . ?
C21B C20B N3 120.08(16) . . ?
C22B C21B C20B 118.81(18) . . ?
C22B C21B H21B 120.6 . . ?
C20B C21B H21B 120.6 . . ?
C23B C22B C21B 123.42(19) . . ?
C23B C22B H22B 118.3 . . ?
C21B C22B H22B 118.3 . . ?
C22B C23B C24B 116.74(19) . . ?
C22B C23B H23B 121.6 . . ?
C24B C23B H23B 121.6 . . ?
F4B C24B C23B 111.5(2) . . ?
F4B C24B C25B 125.6(2) . . ?
C23B C24B C25B 122.81(19) . . ?
C24B C25B C20B 119.33(18) . . ?
C24B C25B H25B 120.3 . . ?
C20B C25B H25B 120.3 . . ?
C8A C7A C12A 119.23(16) . . ?
C8A C7A N1 120.07(14) . . ?
C12A C7A N1 120.63(15) . . ?
C9A C8A C7A 118.53(16) . . ?
C9A C8A H8A 120.7 . . ?
C7A C8A H8A 120.7 . . ?
F2A C9A C8A 118.10(16) . . ?
F2A C9A C10A 118.25(16) . . ?
C8A C9A C10A 123.65(17) . . ?
C9A C10A C11A 117.28(17) . . ?
C9A C10A H10A 121.4 . . ?
C11A C10A H10A 121.4 . . ?
C10A C11A C12A 121.13(16) . . ?
C10A C11A H11A 119.4 . . ?
C12A C11A H11A 119.4 . . ?
C11A C12A C7A 120.17(16) . . ?
C11A C12A H12A 119.9 . . ?
C7A C12A H12A 119.9 . . ?
C12B C7B C8B 119.23(16) . . ?
C12B C7B N1 120.07(14) . . ?
C8B C7B N1 120.63(15) . . ?
C9B C8B C7B 120.17(16) . . ?
C9B C8B H8B 119.9 . . ?
C7B C8B H8B 119.9 . . ?
F2B C9B C10B 117.4(11) . . ?
F2B C9B C8B 121.4(11) . . ?
C10B C9B C8B 121.13(16) . . ?
C11B C10B C9B 117.28(17) . . ?
C11B C10B H10B 121.4 . . ?
C9B C10B H10B 121.4 . . ?
C12B C11B C10B 123.65(17) . . ?
C12B C11B H11B 118.2 . . ?
C10B C11B H11B 118.2 . . ?
C11B C12B C7B 118.53(16) . . ?
C11B C12B H12B 120.7 . . ?
C7B C12B H12B 120.7 . . ?
C13 N2 H2A 118.1(12) . . ?
C13 N2 H2B 121.3(13) . . ?
H2A N2 H2B 117.4(18) . . ?
N1 C13 N2 124.53(16) . . ?
N1 C13 C1 118.62(13) . . ?
N2 C13 C1 116.84(14) . . ?
C13 N1 C7A 116.51(13) . . ?
C13 N1 C7B 116.51(13) . . ?
F1 C4 C3 118.90(15) . . ?
F1 C4 C5 118.39(15) . . ?
C3 C4 C5 122.71(16) . . ?
C4 C3 C2 118.55(15) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C2 C1 120.74(15) . . ?
C3 C2 H2 119.6 . . ?
C1 C2 H2 119.6 . . ?
C2 C1 C6 118.69(15) . . ?
C2 C1 C13 121.68(14) . . ?
C6 C1 C13 119.62(13) . . ?
C5 C6 C1 121.00(14) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C4 C5 C6 118.29(15) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C26 N3 C20A 116.68(13) . . ?
C26 N3 C20B 116.68(13) . . ?
C26 N4 H4B 120.6(14) . . ?
C26 N4 H4A 116.7(14) . . ?
H4B N4 H4A 123(2) . . ?
N3 C26 N4 124.08(17) . . ?
N3 C26 C14 119.29(14) . . ?
N4 C26 C14 116.63(15) . . ?
C15 C14 C19 118.41(17) . . ?
C15 C14 C26 120.81(15) . . ?
C19 C14 C26 120.78(15) . . ?
C18 C19 C14 120.97(16) . . ?
C18 C19 H19 119.5 . . ?
C14 C19 H19 119.5 . . ?
C17 C18 C19 118.39(17) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
F3 C17 C16 118.67(17) . . ?
F3 C17 C18 118.64(17) . . ?
C16 C17 C18 122.69(18) . . ?
C16 C15 C14 121.22(16) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C17 C16 C15 118.30(17) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?

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
C25A C20A C21A C22A -0.7(2) . . . . ?
N3 C20A C21A C22A -177.61(15) . . . . ?
C20A C21A C22A C23A -0.4(3) . . . . ?
C21A C22A C23A C24A 0.9(3) . . . . ?
C22A C23A C24A F4A -178.96(19) . . . . ?
C22A C23A C24A C25A -0.2(3) . . . . ?
F4A C24A C25A C20A 177.75(19) . . . . ?
C23A C24A C25A C20A -0.8(3) . . . . ?
C21A C20A C25A C24A 1.3(2) . . . . ?
N3 C20A C25A C24A 178.24(14) . . . . ?
C25B C20B C21B C22B 1.3(2) . . . . ?
N3 C20B C21B C22B 178.24(14) . . . . ?
C20B C21B C22B C23B -0.8(3) . . . . ?
C21B C22B C23B C24B -0.2(3) . . . . ?
C22B C23B C24B F4B -175.2(2) . . . . ?
C22B C23B C24B C25B 0.9(3) . . . . ?
F4B C24B C25B C20B 175.0(2) . . . . ?
C23B C24B C25B C20B -0.4(3) . . . . ?
C21B C20B C25B C24B -0.7(2) . . . . ?
N3 C20B C25B C24B -177.61(15) . . . . ?
C12A C7A C8A C9A 0.6(2) . . . . ?
N1 C7A C8A C9A 177.42(14) . . . . ?
C7A C8A C9A F2A 179.96(15) . . . . ?
C7A C8A C9A C10A 0.2(3) . . . . ?
F2A C9A C10A C11A 179.66(16) . . . . ?
C8A C9A C10A C11A -0.6(3) . . . . ?
C9A C10A C11A C12A 0.2(3) . . . . ?
C10A C11A C12A C7A 0.6(2) . . . . ?
C8A C7A C12A C11A -1.0(2) . . . . ?
N1 C7A C12A C11A -177.83(14) . . . . ?
C12B C7B C8B C9B -1.0(2) . . . . ?
N1 C7B C8B C9B -177.83(14) . . . . ?
C7B C8B C9B F2B -175.0(16) . . . . ?
C7B C8B C9B C10B 0.6(2) . . . . ?
F2B C9B C10B C11B 176.0(16) . . . . ?
C8B C9B C10B C11B 0.2(3) . . . . ?
C9B C10B C11B C12B -0.6(3) . . . . ?
C10B C11B C12B C7B 0.2(3) . . . . ?
C8B C7B C12B C11B 0.6(2) . . . . ?
N1 C7B C12B C11B 177.42(14) . . . . ?
N2 C13 N1 C7A 5.1(2) . . . . ?
C1 C13 N1 C7A -176.14(13) . . . . ?
N2 C13 N1 C7B 5.1(2) . . . . ?
C1 C13 N1 C7B -176.14(13) . . . . ?
C8A C7A N1 C13 89.75(18) . . . . ?
C12A C7A N1 C13 -93.46(18) . . . . ?
C12B C7B N1 C13 89.75(18) . . . . ?
C8B C7B N1 C13 -93.46(18) . . . . ?
F1 C4 C3 C2 179.73(14) . . . . ?
C5 C4 C3 C2 0.3(3) . . . . ?
C4 C3 C2 C1 -0.4(2) . . . . ?
C3 C2 C1 C6 -0.1(2) . . . . ?
C3 C2 C1 C13 -179.13(14) . . . . ?
N1 C13 C1 C2 -150.31(15) . . . . ?
N2 C13 C1 C2 28.5(2) . . . . ?
N1 C13 C1 C6 30.7(2) . . . . ?
N2 C13 C1 C6 -150.48(15) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C13 C1 C6 C5 179.84(14) . . . . ?
F1 C4 C5 C6 -179.06(14) . . . . ?
C3 C4 C5 C6 0.4(2) . . . . ?
C1 C6 C5 C4 -1.0(2) . . . . ?
C21A C20A N3 C26 -86.30(19) . . . . ?
C25A C20A N3 C26 96.81(18) . . . . ?
C25B C20B N3 C26 -86.30(19) . . . . ?
C21B C20B N3 C26 96.81(18) . . . . ?
C20A N3 C26 N4 -0.7(2) . . . . ?
C20B N3 C26 N4 -0.7(2) . . . . ?
C20A N3 C26 C14 179.20(13) . . . . ?
C20B N3 C26 C14 179.20(13) . . . . ?
N3 C26 C14 C15 151.48(16) . . . . ?
N4 C26 C14 C15 -28.6(2) . . . . ?
N3 C26 C14 C19 -28.2(2) . . . . ?
N4 C26 C14 C19 151.71(15) . . . . ?
C15 C14 C19 C18 0.7(2) . . . . ?
C26 C14 C19 C18 -179.60(15) . . . . ?
C14 C19 C18 C17 0.5(3) . . . . ?
C19 C18 C17 F3 179.23(15) . . . . ?
C19 C18 C17 C16 -1.3(3) . . . . ?
C19 C14 C15 C16 -1.2(2) . . . . ?
C26 C14 C15 C16 179.09(16) . . . . ?
F3 C17 C16 C15 -179.71(16) . . . . ?
C18 C17 C16 C15 0.8(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?

_refine_diff_density_max         0.276
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_DB32W
_database_code_depnum_ccdc_archive 'CCDC 1496291'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2016-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C13 H10 N2 F2), H2 O'
_chemical_formula_sum            'C26 H22 F4 N4 O'
_chemical_formula_weight         482.47

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.8216(3)
_cell_length_b                   11.6073(4)
_cell_length_c                   12.2477(4)
_cell_angle_alpha                105.726(2)
_cell_angle_beta                 111.7750(10)
_cell_angle_gamma                105.364(2)
_cell_volume                     1139.00(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    15370
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      30.17

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   0.648
_exptl_transmission_factor_max   0.795
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18960
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_av_R_equivalents  0.0236
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.965
_diffrn_reflns_theta_max         27.477
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5188
_reflns_number_gt                4623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0419P)²+0.4688P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5188
_refine_ls_number_parameters     348
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F2A F 0.50171(10) 0.85186(9) -0.11495(7) 0.0330(2) Uani 0.9326(18) 1 d . . P A
1
C7A C 0.76385(14) 0.91836(11) 0.21405(11) 0.0181(2) Uani 0.9326(18) 1 d . . P A
1
C8A C 0.63131(14) 0.90391(11) 0.10634(11) 0.0208(2) Uani 0.9326(18) 1 d . . P A
1
H8A H 0.5441 0.9194 0.1136 0.025 Uiso 0.9326(18) 1 calc R U P A 1
C9A C 0.63067(15) 0.86660(12) -0.01071(11) 0.0235(3) Uani 0.9326(18) 1 d . . P
A 1
C10A C 0.75194(16) 0.84157(13) -0.02838(12) 0.0266(3) Uani 0.9326(18) 1 d . . P
A 1
H10A H 0.7467 0.8156 -0.1109 0.032 Uiso 0.9326(18) 1 calc R U P A 1
C11A C 0.88221(17) 0.85589(13) 0.07933(13) 0.0280(3) Uani 0.9326(18) 1 d . . P
A 1
H11A H 0.9681 0.8392 0.0707 0.034 Uiso 0.9326(18) 1 calc R U P A 1
C12A C 0.88914(15) 0.89427(12) 0.19957(12) 0.0233(3) Uani 0.9326(18) 1 d . . P
A 1
H12A H 0.9798 0.9042 0.2724 0.028 Uiso 0.9326(18) 1 calc R U P A 1
F2B F 0.9777(14) 0.8353(13) 0.0505(10) 0.0330(2) Uani 0.0674(18) 1 d . . P A 2
C7B C 0.76385(14) 0.91836(11) 0.21405(11) 0.0181(2) Uani 0.0674(18) 1 d . . P A
2
C8B C 0.88914(15) 0.89427(12) 0.19957(12) 0.0233(3) Uani 0.0674(18) 1 d . . P A
2
H8B H 0.9798 0.9042 0.2724 0.028 Uiso 0.0674(18) 1 calc R U P A 2
C9B C 0.88221(17) 0.85589(13) 0.07933(13) 0.0280(3) Uani 0.0674(18) 1 d . . P A
2
C10B C 0.75194(16) 0.84157(13) -0.02838(12) 0.0266(3) Uani 0.0674(18) 1 d . . P
A 2
H10B H 0.7467 0.8156 -0.1109 0.032 Uiso 0.0674(18) 1 calc R U P A 2
C11B C 0.63067(15) 0.86660(12) -0.01071(11) 0.0235(3) Uani 0.0674(18) 1 d . . P
A 2
H11B H 0.5410 0.8576 -0.0837 0.028 Uiso 0.0674(18) 1 calc R U P A 2
C12B C 0.63131(14) 0.90391(11) 0.10634(11) 0.0208(2) Uani 0.0674(18) 1 d . . P
A 2
H12B H 0.5441 0.9194 0.1136 0.025 Uiso 0.0674(18) 1 calc R U P A 2
F4A F 1.18617(11) 0.53034(9) 0.76857(8) 0.0351(2) Uani 0.9737(19) 1 d . . P B 1
C20A C 0.87668(14) 0.63360(11) 0.61611(11) 0.0181(2) Uani 0.9737(19) 1 d . . P
B 1
C21A C 0.96633(15) 0.55853(11) 0.63456(11) 0.0205(2) Uani 0.9737(19) 1 d . . P
B 1
H21A H 0.9368 0.4783 0.5665 0.025 Uiso 0.9737(19) 1 calc R U P B 1
C22A C 1.09836(15) 0.60278(13) 0.75317(12) 0.0236(3) Uani 0.9737(19) 1 d . . P
B 1
C23A C 1.14521(15) 0.71705(13) 0.85622(11) 0.0240(3) Uani 0.9737(19) 1 d . . P
B 1
H23A H 1.2359 0.7443 0.9372 0.029 Uiso 0.9737(19) 1 calc R U P B 1
C24A C 1.05495(15) 0.79093(12) 0.83732(11) 0.0231(3) Uani 0.9737(19) 1 d . . P
B 1
H24A H 1.0845 0.8702 0.9065 0.028 Uiso 0.9737(19) 1 calc R U P B 1
C25A C 0.92240(15) 0.75061(11) 0.71890(11) 0.0206(2) Uani 0.9737(19) 1 d . . P
B 1
H25A H 0.8625 0.8026 0.7075 0.025 Uiso 0.9737(19) 1 calc R U P B 1
F4B F 1.084(4) 0.881(3) 0.932(3) 0.0351(2) Uani 0.0263(19) 1 d . . P B 2
C20B C 0.87668(14) 0.63360(11) 0.61611(11) 0.0181(2) Uani 0.0263(19) 1 d . . P
B 2
C21B C 0.92240(15) 0.75061(11) 0.71890(11) 0.0206(2) Uani 0.0263(19) 1 d . . P
B 2
H21B H 0.8625 0.8026 0.7075 0.025 Uiso 0.0263(19) 1 calc R U P B 2
C22B C 1.05495(15) 0.79093(12) 0.83732(11) 0.0231(3) Uani 0.0263(19) 1 d . . P
B 2
C23B C 1.14521(15) 0.71705(13) 0.85622(11) 0.0240(3) Uani 0.0263(19) 1 d . . P
B 2
H23B H 1.2359 0.7443 0.9372 0.029 Uiso 0.0263(19) 1 calc R U P B 2
C24B C 1.09836(15) 0.60278(13) 0.75317(12) 0.0236(3) Uani 0.0263(19) 1 d . . P
B 2
H24B H 1.1600 0.5521 0.7645 0.028 Uiso 0.0263(19) 1 calc R U P B 2
C25B C 0.96633(15) 0.55853(11) 0.63456(11) 0.0205(2) Uani 0.0263(19) 1 d . . P
B 2
H25B H 0.9368 0.4783 0.5665 0.025 Uiso 0.0263(19) 1 calc R U P B 2
F1 F 0.69000(10) 1.09446(8) 0.83552(7) 0.03306(19) Uani 1 1 d . . . . .
F3 F 0.13514(9) 0.46557(8) -0.01633(7) 0.03323(19) Uani 1 1 d . . . . .
O1W O 0.58704(12) 0.31488(9) 0.37619(9) 0.0293(2) Uani 1 1 d D . . . .
N4 N 0.84430(13) 0.75727(10) 0.44734(10) 0.0201(2) Uani 1 1 d . . . . .
H4A H 0.935(2) 0.7848(15) 0.5135(16) 0.025(4) Uiso 1 1 d . . . . .
H4B H 0.8211(19) 0.8107(16) 0.4097(15) 0.029(4) Uiso 1 1 d . . . . .
N1 N 0.76598(12) 0.94397(9) 0.33468(9) 0.0183(2) Uani 1 1 d . . . . .
N2 N 0.76105(13) 1.15116(10) 0.35730(10) 0.0213(2) Uani 1 1 d . . . . .
H2A H 0.763(2) 1.1418(16) 0.2861(17) 0.033(4) Uiso 1 1 d . . . . .
H2B H 0.715(2) 1.2045(16) 0.3801(16) 0.033(4) Uiso 1 1 d . . . . .
N3 N 0.73570(12) 0.58451(9) 0.49731(9) 0.0193(2) Uani 1 1 d . . . . .
C19 C 0.56293(14) 0.61768(11) 0.19794(11) 0.0197(2) Uani 1 1 d . . . . .
H19 H 0.6602 0.6602 0.1982 0.024 Uiso 1 1 calc R U . . .
C2 C 0.66027(14) 0.95149(11) 0.52255(11) 0.0181(2) Uani 1 1 d . . . . .
H2 H 0.6193 0.8676 0.4550 0.022 Uiso 1 1 calc R U . . .
C4 C 0.70409(15) 1.08444(13) 0.72706(11) 0.0223(2) Uani 1 1 d . . . . .
C18 C 0.41721(15) 0.57234(12) 0.08802(11) 0.0221(2) Uani 1 1 d . . . . .
H18 H 0.4132 0.5834 0.0130 0.027 Uiso 1 1 calc R U . . .
C3 C 0.64427(14) 0.96063(12) 0.63200(11) 0.0211(2) Uani 1 1 d . . . . .
H3 H 0.5940 0.8845 0.6412 0.025 Uiso 1 1 calc R U . . .
C13 C 0.75227(13) 1.04874(11) 0.39152(10) 0.0166(2) Uani 1 1 d . . . . .
C1 C 0.73556(13) 1.06349(11) 0.51002(10) 0.0168(2) Uani 1 1 d . . . . .
C17 C 0.27845(15) 0.51080(12) 0.09068(11) 0.0221(2) Uani 1 1 d . . . . .
C6 C 0.79324(14) 1.18679(11) 0.60845(11) 0.0205(2) Uani 1 1 d . . . . .
H6 H 0.8434 1.2636 0.6001 0.025 Uiso 1 1 calc R U . . .
C26 C 0.72456(14) 0.65019(11) 0.42616(11) 0.0175(2) Uani 1 1 d . . . . .
C14 C 0.56833(14) 0.60161(10) 0.30806(11) 0.0174(2) Uani 1 1 d . . . . .
C5 C 0.77765(15) 1.19767(12) 0.71870(11) 0.0237(3) Uani 1 1 d . . . . .
H5 H 0.8168 1.2811 0.7863 0.028 Uiso 1 1 calc R U . . .
C15 C 0.42492(15) 0.53868(11) 0.30678(11) 0.0208(2) Uani 1 1 d . . . . .
H15 H 0.4277 0.5271 0.3813 0.025 Uiso 1 1 calc R U . . .
C16 C 0.27856(15) 0.49297(12) 0.19758(12) 0.0236(3) Uani 1 1 d . . . . .
H16 H 0.1807 0.4504 0.1964 0.028 Uiso 1 1 calc R U . . .
H1W H 0.624(2) 0.3981(9) 0.4142(15) 0.042(5) Uiso 1 1 d D . . . .
H2W H 0.551(3) 0.302(2) 0.2973(10) 0.063(6) Uiso 1 1 d 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
F2A C9A 1.3530(14) . ?
C7A C12A 1.3932(17) . ?
C7A C8A 1.3976(17) . ?
C7A N1 1.4168(14) . ?
C8A C9A 1.3777(17) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.3749(18) . ?
C10A C11A 1.3861(19) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.3877(17) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
F2B C9B 1.175(12) . ?
C7B C8B 1.3932(17) . ?
C7B C12B 1.3976(17) . ?
C7B N1 1.4168(14) . ?
C8B C9B 1.3877(17) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.3861(19) . ?
C10B C11B 1.3749(18) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.3777(17) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
F4A C22A 1.3549(14) . ?
C20A C21A 1.3969(16) . ?
C20A C25A 1.4007(16) . ?
C20A N3 1.4131(15) . ?
C21A C22A 1.3787(17) . ?
C21A H21A 0.9500 . ?
C22A C23A 1.3792(18) . ?
C23A C24A 1.3903(18) . ?
C23A H23A 0.9500 . ?
C24A C25A 1.3876(17) . ?
C24A H24A 0.9500 . ?
C25A H25A 0.9500 . ?
F4B C22B 1.21(3) . ?
C20B C25B 1.3969(16) . ?
C20B C21B 1.4007(16) . ?
C20B N3 1.4131(15) . ?
C21B C22B 1.3876(17) . ?
C21B H21B 0.9500 . ?
C22B C23B 1.3903(18) . ?
C23B C24B 1.3792(18) . ?
C23B H23B 0.9500 . ?
C24B C25B 1.3787(17) . ?
C24B H24B 0.9500 . ?
C25B H25B 0.9500 . ?
F1 C4 1.3633(13) . ?
F3 C17 1.3569(14) . ?
O1W H1W 0.853(9) . ?
O1W H2W 0.849(9) . ?
N4 C26 1.3489(15) . ?
N4 H4A 0.851(17) . ?
N4 H4B 0.895(17) . ?
N1 C13 1.2958(15) . ?
N2 C13 1.3560(15) . ?
N2 H2A 0.857(18) . ?
N2 H2B 0.902(17) . ?
N3 C26 1.2986(15) . ?
C19 C18 1.3874(17) . ?
C19 C14 1.3946(16) . ?
C19 H19 0.9500 . ?
C2 C3 1.3860(16) . ?
C2 C1 1.3941(16) . ?
C2 H2 0.9500 . ?
C4 C5 1.3728(19) . ?
C4 C3 1.3799(17) . ?
C18 C17 1.3778(18) . ?
C18 H18 0.9500 . ?
C3 H3 0.9500 . ?
C13 C1 1.4898(15) . ?
C1 C6 1.3968(15) . ?
C17 C16 1.3795(17) . ?
C6 C5 1.3906(17) . ?
C6 H6 0.9500 . ?
C26 C14 1.4890(16) . ?
C14 C15 1.3964(17) . ?
C5 H5 0.9500 . ?
C15 C16 1.3862(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12A C7A C8A 119.34(11) . . ?
C12A C7A N1 119.15(10) . . ?
C8A C7A N1 121.19(10) . . ?
C9A C8A C7A 118.10(11) . . ?
C9A C8A H8A 120.9 . . ?
C7A C8A H8A 120.9 . . ?
F2A C9A C10A 118.03(11) . . ?
F2A C9A C8A 117.96(11) . . ?
C10A C9A C8A 124.01(12) . . ?
C9A C10A C11A 117.15(11) . . ?
C9A C10A H10A 121.4 . . ?
C11A C10A H10A 121.4 . . ?
C10A C11A C12A 121.04(12) . . ?
C10A C11A H11A 119.5 . . ?
C12A C11A H11A 119.5 . . ?
C11A C12A C7A 120.35(11) . . ?
C11A C12A H12A 119.8 . . ?
C7A C12A H12A 119.8 . . ?
C8B C7B C12B 119.34(11) . . ?
C8B C7B N1 119.15(10) . . ?
C12B C7B N1 121.19(10) . . ?
C9B C8B C7B 120.35(11) . . ?
C9B C8B H8B 119.8 . . ?
C7B C8B H8B 119.8 . . ?
F2B C9B C10B 109.5(5) . . ?
F2B C9B C8B 129.4(5) . . ?
C10B C9B C8B 121.04(12) . . ?
C11B C10B C9B 117.15(11) . . ?
C11B C10B H10B 121.4 . . ?
C9B C10B H10B 121.4 . . ?
C10B C11B C12B 124.01(12) . . ?
C10B C11B H11B 118.0 . . ?
C12B C11B H11B 118.0 . . ?
C11B C12B C7B 118.10(11) . . ?
C11B C12B H12B 120.9 . . ?
C7B C12B H12B 120.9 . . ?
C21A C20A C25A 119.10(11) . . ?
C21A C20A N3 118.96(10) . . ?
C25A C20A N3 121.78(11) . . ?
C22A C21A C20A 118.90(11) . . ?
C22A C21A H21A 120.6 . . ?
C20A C21A H21A 120.6 . . ?
F4A C22A C21A 118.15(11) . . ?
F4A C22A C23A 118.69(11) . . ?
C21A C22A C23A 123.15(11) . . ?
C22A C23A C24A 117.62(11) . . ?
C22A C23A H23A 121.2 . . ?
C24A C23A H23A 121.2 . . ?
C25A C24A C23A 120.99(11) . . ?
C25A C24A H24A 119.5 . . ?
C23A C24A H24A 119.5 . . ?
C24A C25A C20A 120.24(11) . . ?
C24A C25A H25A 119.9 . . ?
C20A C25A H25A 119.9 . . ?
C25B C20B C21B 119.10(11) . . ?
C25B C20B N3 118.96(10) . . ?
C21B C20B N3 121.78(11) . . ?
C22B C21B C20B 120.24(11) . . ?
C22B C21B H21B 119.9 . . ?
C20B C21B H21B 119.9 . . ?
F4B C22B C21B 121.2(14) . . ?
F4B C22B C23B 117.1(14) . . ?
C21B C22B C23B 120.99(11) . . ?
C24B C23B C22B 117.62(11) . . ?
C24B C23B H23B 121.2 . . ?
C22B C23B H23B 121.2 . . ?
C25B C24B C23B 123.15(11) . . ?
C25B C24B H24B 118.4 . . ?
C23B C24B H24B 118.4 . . ?
C24B C25B C20B 118.90(11) . . ?
C24B C25B H25B 120.6 . . ?
C20B C25B H25B 120.6 . . ?
H1W O1W H2W 102.3(17) . . ?
C26 N4 H4A 117.3(10) . . ?
C26 N4 H4B 119.8(10) . . ?
H4A N4 H4B 119.9(15) . . ?
C13 N1 C7A 119.94(10) . . ?
C13 N1 C7B 119.94(10) . . ?
C13 N2 H2A 117.4(11) . . ?
C13 N2 H2B 119.9(11) . . ?
H2A N2 H2B 115.1(15) . . ?
C26 N3 C20A 119.64(10) . . ?
C26 N3 C20B 119.64(10) . . ?
C18 C19 C14 120.77(11) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?
C3 C2 C1 121.00(10) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
F1 C4 C5 118.34(11) . . ?
F1 C4 C3 118.00(11) . . ?
C5 C4 C3 123.65(11) . . ?
C17 C18 C19 118.17(11) . . ?
C17 C18 H18 120.9 . . ?
C19 C18 H18 120.9 . . ?
C4 C3 C2 117.54(11) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
N1 C13 N2 125.79(11) . . ?
N1 C13 C1 117.91(10) . . ?
N2 C13 C1 116.18(10) . . ?
C2 C1 C6 119.38(10) . . ?
C2 C1 C13 119.11(10) . . ?
C6 C1 C13 121.51(10) . . ?
F3 C17 C18 118.78(11) . . ?
F3 C17 C16 118.35(11) . . ?
C18 C17 C16 122.87(11) . . ?
C5 C6 C1 120.32(11) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N3 C26 N4 125.69(11) . . ?
N3 C26 C14 117.84(10) . . ?
N4 C26 C14 116.43(10) . . ?
C19 C14 C15 119.27(11) . . ?
C19 C14 C26 120.88(10) . . ?
C15 C14 C26 119.85(10) . . ?
C4 C5 C6 118.09(11) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C16 C15 C14 120.52(11) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C17 C16 C15 118.40(11) . . ?
C17 C16 H16 120.8 . . ?
C15 C16 H16 120.8 . . ?

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
C12A C7A C8A C9A -0.28(17) . . . . ?
N1 C7A C8A C9A -173.81(11) . . . . ?
C7A C8A C9A F2A 179.58(11) . . . . ?
C7A C8A C9A C10A 0.58(19) . . . . ?
F2A C9A C10A C11A -179.34(12) . . . . ?
C8A C9A C10A C11A -0.3(2) . . . . ?
C9A C10A C11A C12A -0.2(2) . . . . ?
C10A C11A C12A C7A 0.5(2) . . . . ?
C8A C7A C12A C11A -0.22(18) . . . . ?
N1 C7A C12A C11A 173.45(11) . . . . ?
C12B C7B C8B C9B -0.22(18) . . . . ?
N1 C7B C8B C9B 173.45(11) . . . . ?
C7B C8B C9B F2B 177.6(9) . . . . ?
C7B C8B C9B C10B 0.5(2) . . . . ?
F2B C9B C10B C11B -177.9(7) . . . . ?
C8B C9B C10B C11B -0.2(2) . . . . ?
C9B C10B C11B C12B -0.3(2) . . . . ?
C10B C11B C12B C7B 0.58(19) . . . . ?
C8B C7B C12B C11B -0.28(17) . . . . ?
N1 C7B C12B C11B -173.81(11) . . . . ?
C25A C20A C21A C22A -0.73(17) . . . . ?
N3 C20A C21A C22A -176.11(10) . . . . ?
C20A C21A C22A F4A -178.51(11) . . . . ?
C20A C21A C22A C23A 1.27(19) . . . . ?
F4A C22A C23A C24A 178.83(11) . . . . ?
C21A C22A C23A C24A -0.95(19) . . . . ?
C22A C23A C24A C25A 0.11(18) . . . . ?
C23A C24A C25A C20A 0.38(18) . . . . ?
C21A C20A C25A C24A -0.06(17) . . . . ?
N3 C20A C25A C24A 175.18(11) . . . . ?
C25B C20B C21B C22B -0.06(17) . . . . ?
N3 C20B C21B C22B 175.18(11) . . . . ?
C20B C21B C22B F4B -170(2) . . . . ?
C20B C21B C22B C23B 0.38(18) . . . . ?
F4B C22B C23B C24B 170.8(19) . . . . ?
C21B C22B C23B C24B 0.11(18) . . . . ?
C22B C23B C24B C25B -0.95(19) . . . . ?
C23B C24B C25B C20B 1.27(19) . . . . ?
C21B C20B C25B C24B -0.73(17) . . . . ?
N3 C20B C25B C24B -176.11(10) . . . . ?
C12A C7A N1 C13 126.47(12) . . . . ?
C8A C7A N1 C13 -59.99(15) . . . . ?
C8B C7B N1 C13 126.47(12) . . . . ?
C12B C7B N1 C13 -59.99(15) . . . . ?
C21A C20A N3 C26 -119.78(12) . . . . ?
C25A C20A N3 C26 64.98(15) . . . . ?
C25B C20B N3 C26 -119.78(12) . . . . ?
C21B C20B N3 C26 64.98(15) . . . . ?
C14 C19 C18 C17 -0.19(17) . . . . ?
F1 C4 C3 C2 -179.53(10) . . . . ?
C5 C4 C3 C2 0.05(18) . . . . ?
C1 C2 C3 C4 0.63(17) . . . . ?
C7A N1 C13 N2 -11.25(18) . . . . ?
C7B N1 C13 N2 -11.25(18) . . . . ?
C7A N1 C13 C1 172.85(10) . . . . ?
C7B N1 C13 C1 172.85(10) . . . . ?
C3 C2 C1 C6 -1.08(17) . . . . ?
C3 C2 C1 C13 179.05(10) . . . . ?
N1 C13 C1 C2 -30.57(15) . . . . ?
N2 C13 C1 C2 153.13(11) . . . . ?
N1 C13 C1 C6 149.56(11) . . . . ?
N2 C13 C1 C6 -26.74(16) . . . . ?
C19 C18 C17 F3 -179.77(10) . . . . ?
C19 C18 C17 C16 0.21(18) . . . . ?
C2 C1 C6 C5 0.85(17) . . . . ?
C13 C1 C6 C5 -179.28(11) . . . . ?
C20A N3 C26 N4 7.96(17) . . . . ?
C20B N3 C26 N4 7.96(17) . . . . ?
C20A N3 C26 C14 -174.29(10) . . . . ?
C20B N3 C26 C14 -174.29(10) . . . . ?
C18 C19 C14 C15 0.20(17) . . . . ?
C18 C19 C14 C26 180.00(10) . . . . ?
N3 C26 C14 C19 -147.27(11) . . . . ?
N4 C26 C14 C19 30.69(15) . . . . ?
N3 C26 C14 C15 32.52(15) . . . . ?
N4 C26 C14 C15 -149.51(11) . . . . ?
F1 C4 C5 C6 179.31(10) . . . . ?
C3 C4 C5 C6 -0.27(19) . . . . ?
C1 C6 C5 C4 -0.19(18) . . . . ?
C19 C14 C15 C16 -0.23(17) . . . . ?
C26 C14 C15 C16 179.97(10) . . . . ?
F3 C17 C16 C15 179.75(11) . . . . ?
C18 C17 C16 C15 -0.23(19) . . . . ?
C14 C15 C16 C17 0.24(18) . . . . ?

_refine_diff_density_max         0.292
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.045

