# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_t328
_database_code_depnum_ccdc_archive 'CCDC 1541691'
_audit_update_record             
;
2017-06-23 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H5 Br F8 N2 O'
_chemical_formula_weight         437.10

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   16.2793(12)
_cell_length_b                   8.0744(4)
_cell_length_c                   12.2026(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.362(7)
_cell_angle_gamma                90.00
_cell_volume                     1503.75(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             848
_exptl_absorpt_coefficient_mu    2.829
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.4840
_exptl_absorpt_correction_T_max  0.8715
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16423
_diffrn_reflns_av_R_equivalents  0.1043
_diffrn_reflns_av_sigmaI/netI    0.0949
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         30.00
_reflns_number_total             4357
_reflns_number_gt                2683
_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)+(0.0636P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4357
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1062
_refine_ls_R_factor_gt           0.0626
_refine_ls_wR_factor_ref         0.1628
_refine_ls_wR_factor_gt          0.1388
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.67284(3) 0.48712(5) -0.06835(3) 0.03487(16) Uani 1 1 d . . .
F1 F 0.93353(16) 0.4431(3) 0.6785(2) 0.0358(6) Uani 1 1 d . . .
F2 F 0.89725(17) 0.7381(3) 0.7658(2) 0.0470(7) Uani 1 1 d . . .
F3 F 0.99723(16) 0.5896(4) 0.8857(2) 0.0419(6) Uani 1 1 d . . .
F4 F 0.87068(18) 0.6070(4) 0.9025(2) 0.0534(8) Uani 1 1 d . . .
F5 F 0.97554(17) 0.2559(3) 0.8745(2) 0.0463(7) Uani 1 1 d . . .
F6 F 0.8443(2) 0.2724(4) 0.8762(3) 0.0550(8) Uani 1 1 d . . .
F7 F 0.86815(18) 0.1588(4) 0.7305(2) 0.0517(7) Uani 1 1 d . . .
F8 F 0.50802(18) 0.2715(3) 0.1945(2) 0.0473(7) Uani 1 1 d . . .
O1 O 0.52172(19) 0.4385(4) 0.3905(2) 0.0344(7) Uani 1 1 d . . .
N1 N 0.6500(2) 0.5037(4) 0.6050(3) 0.0250(7) Uani 1 1 d . . .
H1N H 0.601(3) 0.524(4) 0.607(4) 0.016(11) Uiso 1 1 d . . .
N2 N 0.7209(2) 0.4984(4) 0.7009(3) 0.0253(7) Uani 1 1 d . . .
C1 C 0.7874(3) 0.4703(5) 0.6622(3) 0.0261(8) Uani 1 1 d . . .
C2 C 0.7570(3) 0.4583(5) 0.5395(3) 0.0263(8) Uani 1 1 d . . .
H2 H 0.7908 0.4388 0.4911 0.032 Uiso 1 1 calc R . .
C3 C 0.6688(3) 0.4806(5) 0.5052(3) 0.0250(8) Uani 1 1 d . . .
C4 C 0.5959(3) 0.4655(5) 0.3922(3) 0.0263(8) Uani 1 1 d . . .
C5 C 0.6168(3) 0.4740(5) 0.2821(3) 0.0258(8) Uani 1 1 d . . .
C6 C 0.6810(3) 0.5781(5) 0.2696(3) 0.0306(9) Uani 1 1 d . . .
H6 H 0.7144 0.6455 0.3335 0.037 Uiso 1 1 calc R . .
C7 C 0.6972(3) 0.5849(5) 0.1644(3) 0.0322(9) Uani 1 1 d . . .
H7 H 0.7408 0.6567 0.1557 0.039 Uiso 1 1 calc R . .
C8 C 0.6477(3) 0.4835(5) 0.0724(3) 0.0266(9) Uani 1 1 d . . .
C9 C 0.5825(3) 0.3811(5) 0.0808(3) 0.0287(9) Uani 1 1 d . . .
H9 H 0.5485 0.3154 0.0164 0.034 Uiso 1 1 calc R . .
C10 C 0.5682(3) 0.3772(5) 0.1859(3) 0.0252(8) Uani 1 1 d . . .
C11 C 0.8791(3) 0.4484(5) 0.7432(3) 0.0308(9) Uani 1 1 d . . .
C12 C 0.8927(3) 0.2820(6) 0.8083(4) 0.0370(10) Uani 1 1 d . . .
C13 C 0.9123(3) 0.5963(6) 0.8275(4) 0.0366(10) 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
Br1 C8 1.899(4) . ?
F1 C11 1.378(5) . ?
F2 C13 1.344(5) . ?
F3 C13 1.317(5) . ?
F4 C13 1.318(5) . ?
F5 C12 1.326(5) . ?
F6 C12 1.328(5) . ?
F7 C12 1.336(5) . ?
F8 C10 1.331(4) . ?
O1 C4 1.221(5) . ?
N1 N2 1.328(5) . ?
N1 C3 1.368(5) . ?
N2 C1 1.342(5) . ?
C1 C2 1.407(5) . ?
C1 C11 1.487(6) . ?
C2 C3 1.361(6) . ?
C3 C4 1.478(6) . ?
C4 C5 1.497(5) . ?
C5 C6 1.391(6) . ?
C5 C10 1.403(5) . ?
C6 C7 1.400(5) . ?
C7 C8 1.396(6) . ?
C8 C9 1.377(6) . ?
C9 C10 1.381(5) . ?
C11 C12 1.538(6) . ?
C11 C13 1.546(6) . ?

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
N2 N1 C3 112.7(4) . . ?
N1 N2 C1 104.8(3) . . ?
N2 C1 C2 111.0(4) . . ?
N2 C1 C11 122.2(3) . . ?
C2 C1 C11 126.8(4) . . ?
C3 C2 C1 105.1(4) . . ?
C2 C3 N1 106.4(3) . . ?
C2 C3 C4 134.0(4) . . ?
N1 C3 C4 119.1(4) . . ?
O1 C4 C3 119.9(3) . . ?
O1 C4 C5 121.6(4) . . ?
C3 C4 C5 118.3(4) . . ?
C6 C5 C10 118.1(4) . . ?
C6 C5 C4 122.6(4) . . ?
C10 C5 C4 119.2(4) . . ?
C5 C6 C7 120.9(4) . . ?
C8 C7 C6 118.3(4) . . ?
C9 C8 C7 122.5(4) . . ?
C9 C8 Br1 119.4(3) . . ?
C7 C8 Br1 118.1(3) . . ?
C8 C9 C10 117.7(4) . . ?
F8 C10 C9 117.0(3) . . ?
F8 C10 C5 120.4(3) . . ?
C9 C10 C5 122.5(4) . . ?
F1 C11 C1 108.7(3) . . ?
F1 C11 C12 105.3(3) . . ?
C1 C11 C12 112.2(4) . . ?
F1 C11 C13 105.0(3) . . ?
C1 C11 C13 112.9(4) . . ?
C12 C11 C13 112.2(4) . . ?
F5 C12 F6 108.0(4) . . ?
F5 C12 F7 107.6(4) . . ?
F6 C12 F7 107.7(4) . . ?
F5 C12 C11 112.7(4) . . ?
F6 C12 C11 111.3(4) . . ?
F7 C12 C11 109.2(4) . . ?
F3 C13 F4 108.9(4) . . ?
F3 C13 F2 106.9(4) . . ?
F4 C13 F2 107.2(4) . . ?
F3 C13 C11 112.7(4) . . ?
F4 C13 C11 111.5(4) . . ?
F2 C13 C11 109.4(4) . . ?

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 C1 -0.3(4) . . . . ?
N1 N2 C1 C2 0.2(4) . . . . ?
N1 N2 C1 C11 -177.4(3) . . . . ?
N2 C1 C2 C3 0.0(5) . . . . ?
C11 C1 C2 C3 177.5(4) . . . . ?
C1 C2 C3 N1 -0.2(4) . . . . ?
C1 C2 C3 C4 -172.0(4) . . . . ?
N2 N1 C3 C2 0.4(4) . . . . ?
N2 N1 C3 C4 173.6(3) . . . . ?
C2 C3 C4 O1 155.5(4) . . . . ?
N1 C3 C4 O1 -15.5(6) . . . . ?
C2 C3 C4 C5 -20.9(6) . . . . ?
N1 C3 C4 C5 168.1(3) . . . . ?
O1 C4 C5 C6 146.9(4) . . . . ?
C3 C4 C5 C6 -36.7(6) . . . . ?
O1 C4 C5 C10 -31.2(6) . . . . ?
C3 C4 C5 C10 145.1(4) . . . . ?
C10 C5 C6 C7 -0.5(6) . . . . ?
C4 C5 C6 C7 -178.7(4) . . . . ?
C5 C6 C7 C8 -0.5(6) . . . . ?
C6 C7 C8 C9 1.8(6) . . . . ?
C6 C7 C8 Br1 -177.7(3) . . . . ?
C7 C8 C9 C10 -1.8(6) . . . . ?
Br1 C8 C9 C10 177.7(3) . . . . ?
C8 C9 C10 F8 -176.7(4) . . . . ?
C8 C9 C10 C5 0.7(6) . . . . ?
C6 C5 C10 F8 177.7(4) . . . . ?
C4 C5 C10 F8 -4.1(6) . . . . ?
C6 C5 C10 C9 0.4(6) . . . . ?
C4 C5 C10 C9 178.7(4) . . . . ?
N2 C1 C11 F1 -172.3(4) . . . . ?
C2 C1 C11 F1 10.5(6) . . . . ?
N2 C1 C11 C12 71.7(5) . . . . ?
C2 C1 C11 C12 -105.5(5) . . . . ?
N2 C1 C11 C13 -56.2(5) . . . . ?
C2 C1 C11 C13 126.6(4) . . . . ?
F1 C11 C12 F5 57.4(4) . . . . ?
C1 C11 C12 F5 175.4(3) . . . . ?
C13 C11 C12 F5 -56.2(5) . . . . ?
F1 C11 C12 F6 179.0(3) . . . . ?
C1 C11 C12 F6 -63.0(5) . . . . ?
C13 C11 C12 F6 65.3(5) . . . . ?
F1 C11 C12 F7 -62.2(4) . . . . ?
C1 C11 C12 F7 55.8(5) . . . . ?
C13 C11 C12 F7 -175.9(3) . . . . ?
F1 C11 C13 F3 -51.4(5) . . . . ?
C1 C11 C13 F3 -169.7(3) . . . . ?
C12 C11 C13 F3 62.4(5) . . . . ?
F1 C11 C13 F4 -174.3(3) . . . . ?
C1 C11 C13 F4 67.4(5) . . . . ?
C12 C11 C13 F4 -60.5(5) . . . . ?
F1 C11 C13 F2 67.3(4) . . . . ?
C1 C11 C13 F2 -51.0(5) . . . . ?
C12 C11 C13 F2 -178.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.82(4) 2.03(5) 2.854(5) 177(4) 3_666

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.493
_refine_diff_density_min         -1.216
_refine_diff_density_rms         0.133
####################################################################### 
# 
# 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_tolm326
_database_code_depnum_ccdc_archive 'CCDC 1541687'
_audit_update_record             
;
2017-06-23 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H6 F8 N2 O'
_chemical_formula_weight         358.20

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'
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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   10.601(2)
_cell_length_b                   12.112(2)
_cell_length_c                   12.616(2)
_cell_angle_alpha                61.588(17)
_cell_angle_beta                 74.909(16)
_cell_angle_gamma                90.027(15)
_cell_volume                     1360.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.748
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9635
_exptl_absorpt_correction_T_max  0.9815
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            9867
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_av_sigmaI/netI    0.1207
_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       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         25.00
_reflns_number_total             4476
_reflns_number_gt                2028
_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)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4476
_refine_ls_number_parameters     433
_refine_ls_number_restraints     61
_refine_ls_R_factor_all          0.1945
_refine_ls_R_factor_gt           0.1166
_refine_ls_wR_factor_ref         0.3496
_refine_ls_wR_factor_gt          0.2876
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_restrained_S_all      0.970
_refine_ls_shift/su_max          0.002
_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
F1A F 0.8163(5) 0.0083(6) 0.7796(6) 0.094(2) Uani 1 1 d D . .
F2A F 0.9374(7) 0.2551(12) 0.6137(6) 0.232(7) Uani 1 1 d DU . .
F3A F 0.9792(5) 0.2127(5) 0.7770(6) 0.0942(18) Uani 1 1 d DU . .
F4A F 0.8549(16) 0.3477(10) 0.712(2) 0.345(12) Uani 1 1 d DU . .
F5A F 0.8073(8) 0.0107(6) 0.9672(6) 0.145(3) Uani 1 1 d DU . .
F6A F 0.6728(14) 0.1733(12) 0.9246(11) 0.369(12) Uani 1 1 d DU . .
F7A F 0.6240(6) -0.0308(5) 0.9537(4) 0.0981(19) Uani 1 1 d DU . .
F8A F 0.0053(4) 0.4706(5) 0.8757(4) 0.0683(13) Uani 1 1 d . . .
O1A O 0.4161(4) 0.3906(4) 0.4664(4) 0.0473(12) Uani 1 1 d . . .
N1A N 0.5780(6) 0.2165(6) 0.5709(5) 0.0632(18) Uani 1 1 d . . .
H1NA H 0.5619 0.2133 0.5074 0.076 Uiso 1 1 calc R . .
N2A N 0.6752(7) 0.1628(7) 0.6215(6) 0.072(2) Uani 1 1 d . . .
C1A C 0.6668(7) 0.1886(8) 0.7149(7) 0.066(2) Uani 1 1 d D . .
C2A C 0.5608(7) 0.2611(7) 0.7261(7) 0.059(2) Uani 1 1 d . . .
H2A H 0.5336 0.2911 0.7845 0.071 Uiso 1 1 calc R . .
C3A C 0.5084(6) 0.2760(6) 0.6307(6) 0.0447(16) Uani 1 1 d . . .
C4A C 0.4059(6) 0.3496(6) 0.5778(6) 0.0418(15) Uani 1 1 d . . .
C5A C 0.3018(6) 0.3805(7) 0.6596(6) 0.0457(16) Uani 1 1 d . . .
C6A C 0.2606(6) 0.3053(7) 0.7945(6) 0.0464(16) Uani 1 1 d . . .
H6A H 0.3034 0.2349 0.8350 0.056 Uiso 1 1 calc R . .
C7A C 0.1592(6) 0.3352(6) 0.8652(6) 0.0437(15) Uani 1 1 d . . .
H7A H 0.1285 0.2826 0.9543 0.052 Uiso 1 1 calc R . .
C8A C 0.1027(6) 0.4405(7) 0.8072(7) 0.0496(17) Uani 1 1 d . . .
C9A C 0.1369(7) 0.5160(7) 0.6754(7) 0.0563(19) Uani 1 1 d . . .
H9A H 0.0928 0.5863 0.6369 0.068 Uiso 1 1 calc R . .
C10A C 0.2366(6) 0.4849(6) 0.6036(6) 0.0490(17) Uani 1 1 d . . .
H10A H 0.2619 0.5353 0.5143 0.059 Uiso 1 1 calc R . .
C11A C 0.7709(6) 0.1221(5) 0.7729(5) 0.196(11) Uani 1 1 d D . .
C12A C 0.7117(7) 0.0695(6) 0.9169(6) 0.267(17) Uani 1 1 d DU . .
C13A C 0.8765(7) 0.2330(6) 0.7301(8) 0.123(6) Uani 1 1 d DU . .
F1B F 0.6809(6) 0.0372(6) 0.4092(5) 0.109(2) Uani 1 1 d . . .
F2B F 0.8860(6) 0.1870(7) 0.3838(6) 0.117(3) Uani 1 1 d . . .
F3B F 0.9591(5) 0.0488(5) 0.3334(5) 0.0846(16) Uani 1 1 d . . .
F4B F 0.9833(5) 0.2438(5) 0.1917(5) 0.0810(14) Uani 1 1 d . . .
F5B F 0.7951(8) -0.0503(5) 0.2623(6) 0.108(2) Uani 1 1 d . . .
F6B F 0.8532(5) 0.1472(5) 0.0915(5) 0.0817(15) Uani 1 1 d . . .
F7B F 0.6364(6) 0.0522(5) 0.2053(6) 0.102(2) Uani 1 1 d . . .
F8B F 0.8092(6) 0.8008(5) -0.4880(4) 0.0948(18) Uani 1 1 d . . .
O1B O 0.5462(4) 0.6197(5) 0.0849(4) 0.0501(12) Uani 1 1 d . . .
N1B N 0.5817(6) 0.3836(6) 0.2469(5) 0.0533(15) Uani 1 1 d . . .
H1NB H 0.5225 0.4185 0.2796 0.064 Uiso 1 1 calc R . .
N2B N 0.6150(6) 0.2709(6) 0.3163(5) 0.0524(15) Uani 1 1 d . . .
C1B C 0.7117(8) 0.2563(7) 0.2299(8) 0.061(2) Uani 1 1 d . . .
C2B C 0.7324(6) 0.3557(7) 0.1102(7) 0.0488(16) Uani 1 1 d . . .
H2B H 0.7925 0.3657 0.0346 0.059 Uiso 1 1 calc R . .
C3B C 0.6460(6) 0.4399(7) 0.1223(6) 0.0447(16) Uani 1 1 d . . .
C4B C 0.6172(6) 0.5657(6) 0.0373(6) 0.0419(15) Uani 1 1 d . . .
C5B C 0.6712(6) 0.6239(6) -0.1008(6) 0.0394(14) Uani 1 1 d . . .
C6B C 0.7171(6) 0.5526(7) -0.1631(6) 0.0449(16) Uani 1 1 d . . .
H6B H 0.7164 0.4637 -0.1160 0.054 Uiso 1 1 calc R . .
C7B C 0.7629(7) 0.6165(7) -0.2945(6) 0.0486(17) Uani 1 1 d . . .
H7B H 0.7946 0.5710 -0.3376 0.058 Uiso 1 1 calc R . .
C8B C 0.7624(10) 0.7434(8) -0.3610(7) 0.073(2) Uani 1 1 d . . .
C9B C 0.7106(11) 0.8157(8) -0.3041(8) 0.087(3) Uani 1 1 d . . .
H9B H 0.7052 0.9031 -0.3532 0.104 Uiso 1 1 calc R . .
C10B C 0.6683(8) 0.7548(7) -0.1747(7) 0.0571(19) Uani 1 1 d . . .
H10B H 0.6361 0.8021 -0.1337 0.069 Uiso 1 1 calc R . .
C11B C 0.7717(8) 0.1354(8) 0.2747(10) 0.068(2) Uani 1 1 d . . .
C12B C 0.7704(10) 0.0697(11) 0.2071(11) 0.088(3) Uani 1 1 d . . .
C13B C 0.9012(8) 0.1501(8) 0.2990(7) 0.057(2) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1A C11A 1.432(5) . ?
F2A C13A 1.333(5) . ?
F3A C13A 1.338(5) . ?
F4A C13A 1.328(5) . ?
F5A C12A 1.358(5) . ?
F6A C12A 1.362(5) . ?
F7A C12A 1.339(5) . ?
F8A C8A 1.335(7) . ?
O1A C4A 1.221(7) . ?
N1A N2A 1.357(8) . ?
N1A C3A 1.364(9) . ?
N2A C1A 1.338(11) . ?
C1A C2A 1.446(10) . ?
C1A C11A 1.504(5) . ?
C2A C3A 1.390(10) . ?
C3A C4A 1.494(9) . ?
C4A C5A 1.483(9) . ?
C5A C10A 1.407(9) . ?
C5A C6A 1.433(9) . ?
C6A C7A 1.375(9) . ?
C7A C8A 1.365(10) . ?
C8A C9A 1.403(10) . ?
C9A C10A 1.381(10) . ?
C11A C13A 1.530(5) . ?
C11A C12A 1.550(5) . ?
F1B C11B 1.565(11) . ?
F2B C13B 1.317(8) . ?
F3B C13B 1.305(8) . ?
F4B C13B 1.342(9) . ?
F5B C12B 1.341(12) . ?
F6B C12B 1.345(12) . ?
F7B C12B 1.444(11) . ?
F8B C8B 1.350(9) . ?
O1B C4B 1.222(7) . ?
N1B N2B 1.334(7) . ?
N1B C3B 1.349(9) . ?
N2B C1B 1.368(10) . ?
C1B C2B 1.370(11) . ?
C1B C11B 1.507(10) . ?
C2B C3B 1.406(9) . ?
C3B C4B 1.477(9) . ?
C4B C5B 1.474(9) . ?
C5B C10B 1.411(9) . ?
C5B C6B 1.431(9) . ?
C6B C7B 1.393(9) . ?
C7B C8B 1.357(11) . ?
C8B C9B 1.407(12) . ?
C9B C10B 1.372(11) . ?
C11B C12B 1.418(13) . ?
C11B C13B 1.511(10) . ?

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
N2A N1A C3A 111.7(6) . . ?
C1A N2A N1A 105.6(6) . . ?
N2A C1A C2A 111.4(6) . . ?
N2A C1A C11A 104.1(6) . . ?
C2A C1A C11A 144.3(7) . . ?
C3A C2A C1A 103.1(6) . . ?
N1A C3A C2A 108.2(6) . . ?
N1A C3A C4A 117.7(6) . . ?
C2A C3A C4A 133.8(6) . . ?
O1A C4A C5A 121.9(6) . . ?
O1A C4A C3A 119.1(6) . . ?
C5A C4A C3A 118.7(6) . . ?
C10A C5A C6A 118.0(6) . . ?
C10A C5A C4A 119.3(6) . . ?
C6A C5A C4A 122.6(6) . . ?
C7A C6A C5A 120.0(6) . . ?
C8A C7A C6A 119.8(6) . . ?
F8A C8A C7A 120.0(6) . . ?
F8A C8A C9A 117.4(7) . . ?
C7A C8A C9A 122.5(6) . . ?
C10A C9A C8A 117.8(7) . . ?
C9A C10A C5A 121.6(6) . . ?
F1A C11A C1A 127.4(6) . . ?
F1A C11A C13A 116.9(5) . . ?
C1A C11A C13A 102.3(5) . . ?
F1A C11A C12A 97.1(4) . . ?
C1A C11A C12A 105.8(5) . . ?
C13A C11A C12A 104.6(6) . . ?
F7A C12A F5A 100.7(6) . . ?
F7A C12A F6A 121.3(9) . . ?
F5A C12A F6A 120.8(7) . . ?
F7A C12A C11A 103.8(4) . . ?
F5A C12A C11A 104.8(4) . . ?
F6A C12A C11A 103.2(4) . . ?
F4A C13A F2A 102.9(13) . . ?
F4A C13A F3A 103.3(5) . . ?
F2A C13A F3A 99.7(6) . . ?
F4A C13A C11A 126.0(8) . . ?
F2A C13A C11A 99.8(5) . . ?
F3A C13A C11A 120.1(6) . . ?
N2B N1B C3B 114.6(6) . . ?
N1B N2B C1B 103.2(6) . . ?
N2B C1B C2B 111.8(6) . . ?
N2B C1B C11B 118.3(7) . . ?
C2B C1B C11B 129.7(8) . . ?
C1B C2B C3B 105.6(6) . . ?
N1B C3B C2B 104.7(6) . . ?
N1B C3B C4B 118.9(6) . . ?
C2B C3B C4B 136.4(6) . . ?
O1B C4B C5B 120.9(6) . . ?
O1B C4B C3B 118.0(6) . . ?
C5B C4B C3B 121.1(6) . . ?
C10B C5B C6B 118.8(6) . . ?
C10B C5B C4B 117.9(6) . . ?
C6B C5B C4B 123.2(6) . . ?
C7B C6B C5B 118.6(6) . . ?
C8B C7B C6B 120.3(6) . . ?
F8B C8B C7B 117.9(7) . . ?
F8B C8B C9B 119.0(7) . . ?
C7B C8B C9B 123.1(7) . . ?
C10B C9B C8B 117.2(8) . . ?
C9B C10B C5B 121.9(7) . . ?
C12B C11B C1B 115.3(8) . . ?
C12B C11B C13B 115.3(7) . . ?
C1B C11B C13B 112.6(6) . . ?
C12B C11B F1B 101.4(7) . . ?
C1B C11B F1B 107.9(6) . . ?
C13B C11B F1B 102.5(7) . . ?
F5B C12B F6B 115.3(9) . . ?
F5B C12B C11B 115.7(8) . . ?
F6B C12B C11B 104.1(9) . . ?
F5B C12B F7B 101.7(8) . . ?
F6B C12B F7B 112.4(8) . . ?
C11B C12B F7B 107.6(8) . . ?
F3B C13B F2B 109.2(6) . . ?
F3B C13B F4B 108.0(6) . . ?
F2B C13B F4B 106.2(7) . . ?
F3B C13B C11B 114.6(7) . . ?
F2B C13B C11B 110.9(6) . . ?
F4B C13B C11B 107.7(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
C3A N1A N2A C1A 0.1(9) . . . . ?
N1A N2A C1A C2A 0.2(9) . . . . ?
N1A N2A C1A C11A 177.2(6) . . . . ?
N2A C1A C2A C3A -0.3(9) . . . . ?
C11A C1A C2A C3A -175.4(10) . . . . ?
N2A N1A C3A C2A -0.3(9) . . . . ?
N2A N1A C3A C4A 174.6(6) . . . . ?
C1A C2A C3A N1A 0.4(8) . . . . ?
C1A C2A C3A C4A -173.4(7) . . . . ?
N1A C3A C4A O1A -24.6(9) . . . . ?
C2A C3A C4A O1A 148.7(8) . . . . ?
N1A C3A C4A C5A 161.0(6) . . . . ?
C2A C3A C4A C5A -25.7(11) . . . . ?
O1A C4A C5A C10A -17.9(10) . . . . ?
C3A C4A C5A C10A 156.4(6) . . . . ?
O1A C4A C5A C6A 159.8(6) . . . . ?
C3A C4A C5A C6A -25.9(10) . . . . ?
C10A C5A C6A C7A 0.8(10) . . . . ?
C4A C5A C6A C7A -176.9(6) . . . . ?
C5A C6A C7A C8A -3.6(10) . . . . ?
C6A C7A C8A F8A -179.2(6) . . . . ?
C6A C7A C8A C9A 5.1(10) . . . . ?
F8A C8A C9A C10A -179.4(6) . . . . ?
C7A C8A C9A C10A -3.5(11) . . . . ?
C8A C9A C10A C5A 0.6(11) . . . . ?
C6A C5A C10A C9A 0.7(10) . . . . ?
C4A C5A C10A C9A 178.5(6) . . . . ?
N2A C1A C11A F1A -30.4(9) . . . . ?
C2A C1A C11A F1A 144.8(11) . . . . ?
N2A C1A C11A C13A 108.2(7) . . . . ?
C2A C1A C11A C13A -76.6(13) . . . . ?
N2A C1A C11A C12A -142.6(6) . . . . ?
C2A C1A C11A C12A 32.6(14) . . . . ?
F1A C11A C12A F7A -57.0(6) . . . . ?
C1A C11A C12A F7A 75.1(7) . . . . ?
C13A C11A C12A F7A -177.3(5) . . . . ?
F1A C11A C12A F5A 48.2(5) . . . . ?
C1A C11A C12A F5A -179.7(6) . . . . ?
C13A C11A C12A F5A -72.0(6) . . . . ?
F1A C11A C12A F6A 175.6(7) . . . . ?
C1A C11A C12A F6A -52.3(8) . . . . ?
C13A C11A C12A F6A 55.3(8) . . . . ?
F1A C11A C13A F4A 176.7(11) . . . . ?
C1A C11A C13A F4A 32.8(13) . . . . ?
C12A C11A C13A F4A -77.4(12) . . . . ?
F1A C11A C13A F2A 62.6(8) . . . . ?
C1A C11A C13A F2A -81.2(7) . . . . ?
C12A C11A C13A F2A 168.6(6) . . . . ?
F1A C11A C13A F3A -44.8(10) . . . . ?
C1A C11A C13A F3A 171.4(7) . . . . ?
C12A C11A C13A F3A 61.2(8) . . . . ?
C3B N1B N2B C1B 2.4(8) . . . . ?
N1B N2B C1B C2B -2.5(8) . . . . ?
N1B N2B C1B C11B -178.4(6) . . . . ?
N2B C1B C2B C3B 1.8(8) . . . . ?
C11B C1B C2B C3B 177.1(7) . . . . ?
N2B N1B C3B C2B -1.4(8) . . . . ?
N2B N1B C3B C4B -179.4(5) . . . . ?
C1B C2B C3B N1B -0.3(7) . . . . ?
C1B C2B C3B C4B 177.2(7) . . . . ?
N1B C3B C4B O1B 7.4(9) . . . . ?
C2B C3B C4B O1B -169.9(7) . . . . ?
N1B C3B C4B C5B -172.0(6) . . . . ?
C2B C3B C4B C5B 10.8(11) . . . . ?
O1B C4B C5B C10B 16.3(9) . . . . ?
C3B C4B C5B C10B -164.4(6) . . . . ?
O1B C4B C5B C6B -159.1(6) . . . . ?
C3B C4B C5B C6B 20.3(9) . . . . ?
C10B C5B C6B C7B 2.9(9) . . . . ?
C4B C5B C6B C7B 178.2(6) . . . . ?
C5B C6B C7B C8B -0.6(10) . . . . ?
C6B C7B C8B F8B 179.3(7) . . . . ?
C6B C7B C8B C9B -3.4(13) . . . . ?
F8B C8B C9B C10B -177.8(8) . . . . ?
C7B C8B C9B C10B 5.0(15) . . . . ?
C8B C9B C10B C5B -2.4(13) . . . . ?
C6B C5B C10B C9B -1.4(11) . . . . ?
C4B C5B C10B C9B -176.9(8) . . . . ?
N2B C1B C11B C12B 126.7(9) . . . . ?
C2B C1B C11B C12B -48.4(12) . . . . ?
N2B C1B C11B C13B -98.2(9) . . . . ?
C2B C1B C11B C13B 86.7(10) . . . . ?
N2B C1B C11B F1B 14.2(9) . . . . ?
C2B C1B C11B F1B -160.9(8) . . . . ?
C1B C11B C12B F5B -165.4(8) . . . . ?
C13B C11B C12B F5B 60.7(13) . . . . ?
F1B C11B C12B F5B -49.2(10) . . . . ?
C1B C11B C12B F6B 67.0(10) . . . . ?
C13B C11B C12B F6B -66.9(10) . . . . ?
F1B C11B C12B F6B -176.8(6) . . . . ?
C1B C11B C12B F7B -52.5(11) . . . . ?
C13B C11B C12B F7B 173.6(8) . . . . ?
F1B C11B C12B F7B 63.7(8) . . . . ?
C12B C11B C13B F3B -42.5(12) . . . . ?
C1B C11B C13B F3B -177.6(7) . . . . ?
F1B C11B C13B F3B 66.8(8) . . . . ?
C12B C11B C13B F2B -166.6(8) . . . . ?
C1B C11B C13B F2B 58.3(11) . . . . ?
F1B C11B C13B F2B -57.3(8) . . . . ?
C12B C11B C13B F4B 77.7(10) . . . . ?
C1B C11B C13B F4B -57.5(9) . . . . ?
F1B C11B C13B F4B -173.1(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1NA N2B 0.88 2.08 2.870(8) 149.8 .
N1B H1NB O1A 0.88 2.19 2.906(7) 138.4 .

_diffrn_measured_fraction_theta_max 0.934
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.934
_refine_diff_density_max         0.805
_refine_diff_density_min         -0.663
_refine_diff_density_rms         0.101
####################################################################### 
# 
# 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_tolm331
_database_code_depnum_ccdc_archive 'CCDC 1541688'
_audit_update_record             
;
2017-06-23 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H5 F7 N2 O2'
_chemical_formula_weight         294.14

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   5.6579(5)
_cell_length_b                   29.090(2)
_cell_length_c                   6.9744(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.142(10)
_cell_angle_gamma                90.00
_cell_volume                     1077.70(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9596
_exptl_absorpt_correction_T_max  0.9897
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10035
_diffrn_reflns_av_R_equivalents  0.0746
_diffrn_reflns_av_sigmaI/netI    0.0727
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         3.19
_diffrn_reflns_theta_max         30.00
_reflns_number_total             3090
_reflns_number_gt                1890
_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)+(0.0686P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3090
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1003
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1533
_refine_ls_wR_factor_gt          0.1311
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_restrained_S_all      0.946
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5309(2) 0.56714(5) 0.4132(2) 0.0389(4) Uani 1 1 d . . .
F2 F 0.1590(3) 0.57005(6) 0.0491(2) 0.0514(5) Uani 1 1 d . . .
F3 F 0.1298(3) 0.51224(5) 0.2308(2) 0.0421(4) Uani 1 1 d . . .
F4 F -0.1258(3) 0.56890(5) 0.1882(2) 0.0413(4) Uani 1 1 d . . .
F5 F 0.3071(3) 0.52271(5) 0.6390(2) 0.0413(4) Uani 1 1 d . . .
F6 F 0.0392(2) 0.57669(5) 0.6069(2) 0.0344(4) Uani 1 1 d . . .
F7 F 0.4326(3) 0.58982(6) 0.7579(2) 0.0499(5) Uani 1 1 d . . .
O1 O 0.7160(3) 0.75418(5) 0.3469(3) 0.0296(4) Uani 1 1 d . . .
O2 O 0.3474(3) 0.78402(5) 0.3431(2) 0.0259(4) Uani 1 1 d . . .
N1 N 0.1492(3) 0.70092(7) 0.3605(3) 0.0237(4) Uani 1 1 d . . .
H1A H 0.051(4) 0.7224(9) 0.358(4) 0.027(6) Uiso 1 1 d . . .
N2 N 0.0848(3) 0.65737(6) 0.3758(3) 0.0255(4) Uani 1 1 d . . .
C1 C 0.2881(4) 0.63296(8) 0.3780(3) 0.0224(4) Uani 1 1 d . . .
C2 C 0.4811(4) 0.66124(8) 0.3651(3) 0.0229(4) Uani 1 1 d . . .
H2 H 0.6422 0.6523 0.3641 0.027 Uiso 1 1 calc R . .
C3 C 0.3851(4) 0.70499(7) 0.3542(3) 0.0225(4) Uani 1 1 d . . .
C4 C 0.5026(4) 0.74958(7) 0.3463(3) 0.0229(4) Uani 1 1 d . . .
C5 C 0.4479(4) 0.82973(8) 0.3428(4) 0.0293(5) Uani 1 1 d . . .
H5A H 0.3253 0.8525 0.3533 0.044 Uiso 1 1 calc R . .
H5B H 0.4816 0.8346 0.2155 0.044 Uiso 1 1 calc R . .
H5C H 0.6047 0.8331 0.4593 0.044 Uiso 1 1 calc R . .
C6 C 0.2957(4) 0.58192(8) 0.4017(3) 0.0254(5) Uani 1 1 d . . .
C7 C 0.2665(4) 0.56709(8) 0.6041(4) 0.0287(5) Uani 1 1 d . . .
C8 C 0.1101(5) 0.55751(8) 0.2154(4) 0.0307(5) 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
F1 C6 1.374(2) . ?
F2 C8 1.333(3) . ?
F3 C8 1.323(3) . ?
F4 C8 1.324(3) . ?
F5 C7 1.319(3) . ?
F6 C7 1.323(3) . ?
F7 C7 1.333(3) . ?
O1 C4 1.213(2) . ?
O2 C4 1.327(3) . ?
O2 C5 1.447(3) . ?
N1 N2 1.333(3) . ?
N1 C3 1.355(3) . ?
N1 H1A 0.83(3) . ?
N2 C1 1.347(3) . ?
C1 C2 1.395(3) . ?
C1 C6 1.493(3) . ?
C2 C3 1.375(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.467(3) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C8 1.535(3) . ?
C6 C7 1.539(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 O2 C5 115.85(17) . . ?
N2 N1 C3 112.64(17) . . ?
N2 N1 H1A 121.1(18) . . ?
C3 N1 H1A 126.3(18) . . ?
N1 N2 C1 104.25(17) . . ?
N2 C1 C2 111.9(2) . . ?
N2 C1 C6 121.18(18) . . ?
C2 C1 C6 126.89(18) . . ?
C3 C2 C1 104.25(18) . . ?
C3 C2 H2 127.9 . . ?
C1 C2 H2 127.9 . . ?
N1 C3 C2 106.98(18) . . ?
N1 C3 C4 122.84(19) . . ?
C2 C3 C4 130.13(19) . . ?
O1 C4 O2 124.7(2) . . ?
O1 C4 C3 124.1(2) . . ?
O2 C4 C3 111.23(18) . . ?
O2 C5 H5A 109.5 . . ?
O2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
O2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
F1 C6 C1 107.96(16) . . ?
F1 C6 C8 105.75(18) . . ?
C1 C6 C8 112.42(19) . . ?
F1 C6 C7 105.43(18) . . ?
C1 C6 C7 111.84(18) . . ?
C8 C6 C7 112.88(18) . . ?
F5 C7 F6 108.21(18) . . ?
F5 C7 F7 107.92(19) . . ?
F6 C7 F7 107.65(19) . . ?
F5 C7 C6 112.12(19) . . ?
F6 C7 C6 111.48(18) . . ?
F7 C7 C6 109.30(18) . . ?
F3 C8 F4 108.27(18) . . ?
F3 C8 F2 107.83(18) . . ?
F4 C8 F2 107.9(2) . . ?
F3 C8 C6 112.2(2) . . ?
F4 C8 C6 111.57(18) . . ?
F2 C8 C6 108.88(19) . . ?

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 C1 -0.4(2) . . . . ?
N1 N2 C1 C2 0.3(2) . . . . ?
N1 N2 C1 C6 177.72(19) . . . . ?
N2 C1 C2 C3 -0.1(2) . . . . ?
C6 C1 C2 C3 -177.4(2) . . . . ?
N2 N1 C3 C2 0.3(2) . . . . ?
N2 N1 C3 C4 -177.34(19) . . . . ?
C1 C2 C3 N1 -0.1(2) . . . . ?
C1 C2 C3 C4 177.3(2) . . . . ?
C5 O2 C4 O1 -0.7(3) . . . . ?
C5 O2 C4 C3 177.84(17) . . . . ?
N1 C3 C4 O1 177.7(2) . . . . ?
C2 C3 C4 O1 0.6(4) . . . . ?
N1 C3 C4 O2 -0.9(3) . . . . ?
C2 C3 C4 O2 -178.0(2) . . . . ?
N2 C1 C6 F1 -175.71(19) . . . . ?
C2 C1 C6 F1 1.3(3) . . . . ?
N2 C1 C6 C8 68.0(3) . . . . ?
C2 C1 C6 C8 -115.0(2) . . . . ?
N2 C1 C6 C7 -60.2(3) . . . . ?
C2 C1 C6 C7 116.8(2) . . . . ?
F1 C6 C7 F5 -54.3(2) . . . . ?
C1 C6 C7 F5 -171.40(18) . . . . ?
C8 C6 C7 F5 60.6(2) . . . . ?
F1 C6 C7 F6 -175.82(17) . . . . ?
C1 C6 C7 F6 67.1(2) . . . . ?
C8 C6 C7 F6 -60.8(2) . . . . ?
F1 C6 C7 F7 65.3(2) . . . . ?
C1 C6 C7 F7 -51.8(2) . . . . ?
C8 C6 C7 F7 -179.73(19) . . . . ?
F1 C6 C8 F3 58.0(2) . . . . ?
C1 C6 C8 F3 175.61(16) . . . . ?
C7 C6 C8 F3 -56.7(2) . . . . ?
F1 C6 C8 F4 179.73(17) . . . . ?
C1 C6 C8 F4 -62.7(2) . . . . ?
C7 C6 C8 F4 65.0(3) . . . . ?
F1 C6 C8 F2 -61.2(2) . . . . ?
C1 C6 C8 F2 56.3(2) . . . . ?
C7 C6 C8 F2 -176.02(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1A O1 0.83(3) 2.09(3) 2.874(2) 158(2) 1_455

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.324
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.076
####################################################################### 
# 
# 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_tolm329
_database_code_depnum_ccdc_archive 'CCDC 1541689'
_audit_update_record             
;
2017-06-23 deposited with the CCDC.
2017-07-14 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 H9 F7 N2 O'
_chemical_formula_weight         318.20

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'
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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   12.6081(12)
_cell_length_b                   16.880(3)
_cell_length_c                   19.0740(16)
_cell_angle_alpha                68.673(13)
_cell_angle_beta                 90.021(8)
_cell_angle_gamma                89.803(11)
_cell_volume                     3781.3(8)
_cell_formula_units_Z            12
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1920
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9651
_exptl_absorpt_correction_T_max  0.9946
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24142
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1629
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         25.00
_reflns_number_total             24236
_reflns_number_gt                11489
_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)+(0.1320P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         24236
_refine_ls_number_parameters     1136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2050
_refine_ls_R_factor_gt           0.1201
_refine_ls_wR_factor_ref         0.3391
_refine_ls_wR_factor_gt          0.2760
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 0.3219(3) 0.0734(2) 0.3296(2) 0.0460(11) Uani 1 1 d . . .
F2A F 0.2086(3) 0.0893(3) 0.4455(2) 0.0675(15) Uani 1 1 d . . .
F3A F 0.3353(3) -0.0029(2) 0.4781(2) 0.0548(12) Uani 1 1 d . . .
F4A F 0.3473(4) 0.1158(3) 0.4952(2) 0.0639(13) Uani 1 1 d . . .
F5A F 0.5097(3) 0.0293(2) 0.3968(2) 0.0440(10) Uani 1 1 d . . .
F6A F 0.5273(3) 0.1502(3) 0.4091(3) 0.0646(13) Uani 1 1 d . . .
F7A F 0.5133(4) 0.1440(3) 0.2986(2) 0.0614(13) Uani 1 1 d . . .
O1A O 0.2090(3) 0.4695(3) 0.1870(2) 0.0321(10) Uani 1 1 d . . .
N1A N 0.3074(4) 0.3446(3) 0.3065(2) 0.0274(12) Uani 1 1 d . . .
H1NA H 0.3137 0.3956 0.3087 0.033 Uiso 1 1 calc R . .
N2A N 0.3510(4) 0.2732(3) 0.3562(3) 0.0315(12) Uani 1 1 d . . .
C1A C 0.3249(5) 0.2107(4) 0.3322(3) 0.0340(16) Uani 1 1 d . . .
C2A C 0.2634(5) 0.2406(3) 0.2671(3) 0.0275(14) Uani 1 1 d . . .
H2A H 0.2353 0.2090 0.2391 0.033 Uiso 1 1 calc R . .
C3A C 0.2524(4) 0.3269(4) 0.2526(3) 0.0233(13) Uani 1 1 d . . .
C4A C 0.2024(5) 0.3961(4) 0.1893(3) 0.0303(14) Uani 1 1 d . . .
C5A C 0.1493(5) 0.3708(4) 0.1311(3) 0.0345(16) Uani 1 1 d . . .
H5A H 0.2032 0.3493 0.1038 0.041 Uiso 1 1 calc R . .
C6A C 0.0574(5) 0.3098(4) 0.1547(4) 0.0436(18) Uani 1 1 d . . .
H6AA H 0.0211 0.3094 0.2009 0.052 Uiso 1 1 calc R . .
H6AB H 0.0750 0.2513 0.1581 0.052 Uiso 1 1 calc R . .
C7A C 0.0003(5) 0.3632(4) 0.0817(4) 0.0429(18) Uani 1 1 d . . .
H7AA H 0.0075 0.3401 0.0411 0.052 Uiso 1 1 calc R . .
H7AB H -0.0749 0.3753 0.0891 0.052 Uiso 1 1 calc R . .
C8A C 0.0732(5) 0.4361(4) 0.0732(3) 0.0393(17) Uani 1 1 d . . .
H8AA H 0.0429 0.4794 0.0912 0.047 Uiso 1 1 calc R . .
H8AB H 0.1036 0.4628 0.0222 0.047 Uiso 1 1 calc R . .
C9A C 0.3596(5) 0.1206(4) 0.3695(3) 0.0311(15) Uani 1 1 d . . .
C10A C 0.4787(6) 0.1095(4) 0.3697(4) 0.0413(17) Uani 1 1 d . . .
C11A C 0.3149(6) 0.0800(5) 0.4485(4) 0.0467(19) Uani 1 1 d . . .
F1B F 0.9595(3) 0.1795(2) -0.0715(2) 0.0418(10) Uani 1 1 d . . .
F2B F 0.7574(4) 0.1638(2) -0.1189(2) 0.0590(12) Uani 1 1 d . . .
F3B F 0.8409(3) 0.0475(2) -0.0643(3) 0.0530(11) Uani 1 1 d . . .
F4B F 0.7148(3) 0.0866(2) -0.0066(2) 0.0497(11) Uani 1 1 d . . .
F5B F 0.9644(4) 0.0378(3) 0.0546(2) 0.0632(13) Uani 1 1 d . . .
F6B F 0.8435(4) 0.0864(2) 0.1062(2) 0.0557(12) Uani 1 1 d . . .
F7B F 0.9918(4) 0.1521(3) 0.0740(3) 0.0659(13) Uani 1 1 d . . .
O1B O 0.6845(4) 0.4793(2) -0.0067(2) 0.0331(10) Uani 1 1 d . . .
N1B N 0.7981(4) 0.3758(3) -0.0626(3) 0.0279(12) Uani 1 1 d . . .
H1NB H 0.8018 0.4302 -0.0905 0.033 Uiso 1 1 calc R . .
N2B N 0.8528(4) 0.3170(3) -0.0764(3) 0.0337(13) Uani 1 1 d . . .
C1B C 0.8260(5) 0.2444(4) -0.0223(3) 0.0309(15) Uani 1 1 d . . .
C2B C 0.7534(5) 0.2573(4) 0.0261(3) 0.0294(14) Uani 1 1 d . . .
H2B H 0.7222 0.2155 0.0689 0.035 Uiso 1 1 calc R . .
C3B C 0.7353(4) 0.3447(4) -0.0011(3) 0.0265(14) Uani 1 1 d . . .
C4B C 0.6711(5) 0.4008(4) 0.0247(4) 0.0344(15) Uani 1 1 d . . .
C5B C 0.5856(6) 0.3663(5) 0.0804(4) 0.0483(19) Uani 1 1 d . . .
H5B H 0.5254 0.3486 0.0552 0.058 Uiso 1 1 calc R . .
C6B C 0.6117(6) 0.2940(4) 0.1529(4) 0.053(2) Uani 1 1 d . . .
H6BA H 0.6867 0.2922 0.1689 0.063 Uiso 1 1 calc R . .
H6BB H 0.5875 0.2376 0.1547 0.063 Uiso 1 1 calc R . .
C7B C 0.5346(6) 0.3386(4) 0.1920(4) 0.0469(19) Uani 1 1 d . . .
H7BA H 0.4627 0.3135 0.2010 0.056 Uiso 1 1 calc R . .
H7BB H 0.5640 0.3433 0.2384 0.056 Uiso 1 1 calc R . .
C8B C 0.5413(6) 0.4206(5) 0.1234(4) 0.055(2) Uani 1 1 d . . .
H8BA H 0.5921 0.4625 0.1290 0.066 Uiso 1 1 calc R . .
H8BB H 0.4717 0.4473 0.1048 0.066 Uiso 1 1 calc R . .
C9B C 0.8760(5) 0.1619(4) -0.0227(3) 0.0289(14) Uani 1 1 d . . .
C10B C 0.9195(6) 0.1092(4) 0.0557(4) 0.0374(16) Uani 1 1 d . . .
C11B C 0.7947(6) 0.1150(4) -0.0533(4) 0.0380(17) Uani 1 1 d . . .
F1C F 0.5298(3) 0.8198(2) 0.2305(2) 0.0509(11) Uani 1 1 d . . .
F2C F 0.7181(4) 0.8378(3) 0.1622(2) 0.0638(13) Uani 1 1 d . . .
F3C F 0.6481(4) 0.9589(3) 0.1515(2) 0.0649(14) Uani 1 1 d . . .
F4C F 0.7797(3) 0.9099(2) 0.2248(2) 0.0474(10) Uani 1 1 d . . .
F5C F 0.5209(3) 0.9619(2) 0.2621(2) 0.0548(11) Uani 1 1 d . . .
F6C F 0.6554(3) 0.9233(2) 0.3365(2) 0.0488(11) Uani 1 1 d . . .
F7C F 0.5088(3) 0.8510(2) 0.3621(2) 0.0592(13) Uani 1 1 d . . .
O1C O 0.8256(4) 0.5305(2) 0.4827(2) 0.0352(11) Uani 1 1 d . . .
N1C N 0.7038(4) 0.6284(3) 0.3629(3) 0.0320(12) Uani 1 1 d . . .
H1NC H 0.7035 0.5737 0.3706 0.038 Uiso 1 1 calc R . .
N2C N 0.6436(4) 0.6863(3) 0.3116(3) 0.0343(13) Uani 1 1 d . . .
C1C C 0.6678(5) 0.7591(4) 0.3172(3) 0.0306(14) Uani 1 1 d . . .
C2C C 0.7463(5) 0.7503(4) 0.3728(3) 0.0312(15) Uani 1 1 d . . .
H2C H 0.7781 0.7931 0.3871 0.037 Uiso 1 1 calc R . .
C3C C 0.7645(5) 0.6637(4) 0.4009(3) 0.0276(14) Uani 1 1 d . . .
C4C C 0.8351(5) 0.6067(4) 0.4636(3) 0.0286(14) Uani 1 1 d . . .
C5C C 0.9152(5) 0.6513(4) 0.4960(3) 0.0367(16) Uani 1 1 d . . .
H5C H 0.9718 0.6784 0.4582 0.044 Uiso 1 1 calc R . .
C6C C 0.8770(6) 0.7123(5) 0.5328(4) 0.051(2) Uani 1 1 d . . .
H6CA H 0.8024 0.7034 0.5500 0.061 Uiso 1 1 calc R . .
H6CB H 0.8905 0.7729 0.5026 0.061 Uiso 1 1 calc R . .
C7C C 0.9597(6) 0.6718(4) 0.5966(4) 0.0475(19) Uani 1 1 d . . .
H7CA H 1.0269 0.7040 0.5897 0.057 Uiso 1 1 calc R . .
H7CB H 0.9311 0.6589 0.6479 0.057 Uiso 1 1 calc R . .
C8C C 0.9659(6) 0.5935(4) 0.5726(4) 0.0462(19) Uani 1 1 d . . .
H8CA H 0.9208 0.5453 0.6028 0.055 Uiso 1 1 calc R . .
H8CB H 1.0391 0.5744 0.5681 0.055 Uiso 1 1 calc R . .
C9C C 0.6171(5) 0.8402(4) 0.2646(4) 0.0341(15) Uani 1 1 d . . .
C10C C 0.5743(6) 0.8943(4) 0.3060(4) 0.0442(18) Uani 1 1 d . . .
C11C C 0.6916(6) 0.8867(4) 0.2000(4) 0.0389(17) Uani 1 1 d . . .
F1D F 0.7708(4) 0.0745(2) 0.3955(3) 0.0730(16) Uani 1 1 d . . .
F2D F 0.9492(5) 0.1202(3) 0.4481(3) 0.0878(18) Uani 1 1 d . . .
F3D F 0.9772(4) 0.0253(3) 0.4018(3) 0.0699(14) Uani 1 1 d . . .
F4D F 1.0267(4) 0.1539(3) 0.3392(3) 0.0736(15) Uani 1 1 d . . .
F5D F 0.8532(3) 0.0284(2) 0.2871(2) 0.0494(10) Uani 1 1 d . . .
F6D F 0.9074(4) 0.1522(3) 0.2232(2) 0.0641(14) Uani 1 1 d . . .
F7D F 0.7418(4) 0.1289(3) 0.2428(3) 0.0674(13) Uani 1 1 d . . .
O1D O 0.7153(4) 0.4731(2) 0.3363(2) 0.0348(11) Uani 1 1 d . . .
N1D N 0.8019(4) 0.3525(3) 0.2854(2) 0.0270(12) Uani 1 1 d . . .
H1ND H 0.8085 0.4046 0.2524 0.032 Uiso 1 1 calc R . .
N2D N 0.8405(5) 0.2834(3) 0.2756(3) 0.0393(14) Uani 1 1 d . . .
C1D C 0.8129(5) 0.2182(4) 0.3370(4) 0.0359(16) Uani 1 1 d . . .
C2D C 0.7590(5) 0.2449(4) 0.3871(3) 0.0256(13) Uani 1 1 d . . .
H2D H 0.7329 0.2103 0.4352 0.031 Uiso 1 1 calc R . .
C3D C 0.7505(5) 0.3320(4) 0.3533(4) 0.0314(15) Uani 1 1 d . . .
C4D C 0.7049(5) 0.3979(4) 0.3782(3) 0.0277(14) Uani 1 1 d . . .
C5D C 0.6531(5) 0.3706(4) 0.4510(4) 0.0363(16) Uani 1 1 d . . .
H5D H 0.7069 0.3474 0.4920 0.044 Uiso 1 1 calc R . .
C6D C 0.5557(5) 0.3106(4) 0.4670(4) 0.0371(16) Uani 1 1 d . . .
H6DA H 0.5169 0.3132 0.4211 0.045 Uiso 1 1 calc R . .
H6DB H 0.5722 0.2510 0.4992 0.045 Uiso 1 1 calc R . .
C7D C 0.5032(6) 0.3612(4) 0.5092(4) 0.0485(19) Uani 1 1 d . . .
H7DA H 0.5134 0.3364 0.5644 0.058 Uiso 1 1 calc R . .
H7DB H 0.4277 0.3749 0.4960 0.058 Uiso 1 1 calc R . .
C8D C 0.5802(5) 0.4346(4) 0.4683(4) 0.0379(16) Uani 1 1 d . . .
H8DA H 0.5495 0.4785 0.4229 0.045 Uiso 1 1 calc R . .
H8DB H 0.6129 0.4609 0.5017 0.045 Uiso 1 1 calc R . .
C9D C 0.8441(6) 0.1289(4) 0.3472(4) 0.0406(17) Uani 1 1 d . . .
C10D C 0.8371(5) 0.1082(4) 0.2735(4) 0.0362(17) Uani 1 1 d . . .
C11D C 0.9533(6) 0.1055(5) 0.3848(4) 0.0453(18) Uani 1 1 d . . .
F1E F 0.7218(3) 0.9002(2) -0.0125(2) 0.0466(11) Uani 1 1 d . . .
F2E F 0.5387(3) 0.8388(3) 0.0572(2) 0.0543(12) Uani 1 1 d . . .
F3E F 0.5187(3) 0.9444(2) -0.0467(2) 0.0503(11) Uani 1 1 d . . .
F4E F 0.4772(3) 0.8198(3) -0.0419(3) 0.0578(12) Uani 1 1 d . . .
F5E F 0.6580(4) 0.9618(2) -0.1551(2) 0.0592(13) Uani 1 1 d . . .
F6E F 0.6130(4) 0.8404(3) -0.1553(2) 0.0580(12) Uani 1 1 d . . .
F7E F 0.7766(3) 0.8660(3) -0.1383(2) 0.0616(13) Uani 1 1 d . . .
O1E O 0.8103(4) 0.5024(2) 0.1519(2) 0.0362(11) Uani 1 1 d . . .
N1E N 0.7020(4) 0.6248(3) 0.0333(2) 0.0261(11) Uani 1 1 d . . .
H1NE H 0.6888 0.5726 0.0361 0.031 Uiso 1 1 calc R . .
N2E N 0.6531(4) 0.6940(3) -0.0143(3) 0.0269(11) Uani 1 1 d . . .
C1E C 0.6958(5) 0.7579(4) -0.0005(3) 0.0325(15) Uani 1 1 d . . .
C2E C 0.7726(5) 0.7311(3) 0.0570(3) 0.0288(14) Uani 1 1 d . . .
H2E H 0.8132 0.7652 0.0772 0.035 Uiso 1 1 calc R . .
C3E C 0.7753(5) 0.6452(3) 0.0771(3) 0.0219(13) Uani 1 1 d . . .
C4E C 0.8344(5) 0.5770(4) 0.1372(3) 0.0330(15) Uani 1 1 d . . .
C5E C 0.9230(5) 0.6066(4) 0.1745(3) 0.0294(14) Uani 1 1 d . . .
H5E H 0.9797 0.6335 0.1368 0.035 Uiso 1 1 calc R . .
C6E C 0.8951(6) 0.6652(4) 0.2175(4) 0.0417(17) Uani 1 1 d . . .
H6EA H 0.8221 0.6580 0.2379 0.050 Uiso 1 1 calc R . .
H6EB H 0.9114 0.7260 0.1897 0.050 Uiso 1 1 calc R . .
C7E C 0.9816(6) 0.6164(4) 0.2761(4) 0.0474(19) Uani 1 1 d . . .
H7EA H 1.0516 0.6447 0.2675 0.057 Uiso 1 1 calc R . .
H7EB H 0.9591 0.6008 0.3292 0.057 Uiso 1 1 calc R . .
C8E C 0.9732(6) 0.5435(4) 0.2464(3) 0.0382(16) Uani 1 1 d . . .
H8EA H 1.0425 0.5206 0.2382 0.046 Uiso 1 1 calc R . .
H8EB H 0.9250 0.4972 0.2760 0.046 Uiso 1 1 calc R . .
C9E C 0.6596(5) 0.8482(4) -0.0379(3) 0.0341(16) Uani 1 1 d . . .
C10E C 0.6770(6) 0.8792(4) -0.1248(4) 0.050(2) Uani 1 1 d . . .
C11E C 0.5468(6) 0.8631(4) -0.0166(4) 0.0381(17) Uani 1 1 d . . .
F1F F 0.2393(3) 0.8940(2) 0.2663(2) 0.0495(11) Uani 1 1 d . . .
F2F F 0.0565(4) 0.8375(3) 0.2214(3) 0.0674(13) Uani 1 1 d . . .
F3F F 0.0345(4) 0.9429(3) 0.2568(3) 0.0609(12) Uani 1 1 d . . .
F4F F -0.0170(3) 0.8210(3) 0.3268(3) 0.0670(14) Uani 1 1 d . . .
F5F F 0.1589(4) 0.9488(3) 0.3696(3) 0.0593(12) Uani 1 1 d . . .
F6F F 0.1078(4) 0.8223(3) 0.4402(2) 0.0661(14) Uani 1 1 d . . .
F7F F 0.2743(4) 0.8504(3) 0.4165(3) 0.0635(13) Uani 1 1 d . . .
O1F O 0.3112(4) 0.4937(2) 0.3474(2) 0.0337(10) Uani 1 1 d . . .
N1F N 0.2006(4) 0.6157(3) 0.3859(3) 0.0287(12) Uani 1 1 d . . .
H1NF H 0.1851 0.5635 0.4156 0.034 Uiso 1 1 calc R . .
N2F N 0.1522(4) 0.6856(3) 0.3900(3) 0.0313(12) Uani 1 1 d . . .
C1F C 0.1984(5) 0.7494(4) 0.3364(3) 0.0299(14) Uani 1 1 d . . .
C2F C 0.2756(5) 0.7219(4) 0.2990(4) 0.0358(16) Uani 1 1 d . . .
H2F H 0.3196 0.7562 0.2592 0.043 Uiso 1 1 calc R . .
C3F C 0.2756(5) 0.6349(3) 0.3313(3) 0.0238(13) Uani 1 1 d . . .
C4F C 0.3345(6) 0.5693(4) 0.3161(3) 0.0325(15) Uani 1 1 d . . .
C5F C 0.4234(5) 0.5984(4) 0.2623(3) 0.0315(14) Uani 1 1 d . . .
H5F H 0.4815 0.6199 0.2863 0.038 Uiso 1 1 calc R . .
C6F C 0.4060(6) 0.6617(4) 0.1822(4) 0.0426(18) Uani 1 1 d . . .
H6FA H 0.4261 0.7208 0.1751 0.051 Uiso 1 1 calc R . .
H6FB H 0.3339 0.6597 0.1623 0.051 Uiso 1 1 calc R . .
C7F C 0.4899(5) 0.6140(4) 0.1543(4) 0.0417(17) Uani 1 1 d . . .
H7FA H 0.5619 0.6384 0.1499 0.050 Uiso 1 1 calc R . .
H7FB H 0.4694 0.6045 0.1079 0.050 Uiso 1 1 calc R . .
C8F C 0.4718(6) 0.5367(4) 0.2270(4) 0.0438(17) Uani 1 1 d . . .
H8FA H 0.5380 0.5083 0.2517 0.053 Uiso 1 1 calc R . .
H8FB H 0.4207 0.4949 0.2214 0.053 Uiso 1 1 calc R . .
C9F C 0.1684(5) 0.8410(4) 0.3190(3) 0.0358(16) Uani 1 1 d . . .
C10F C 0.1777(6) 0.8681(5) 0.3860(4) 0.049(2) Uani 1 1 d . . .
C11F C 0.0582(6) 0.8620(4) 0.2807(4) 0.0404(17) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1A C9A 1.374(7) . ?
F2A C11A 1.348(8) . ?
F3A C11A 1.329(8) . ?
F4A C11A 1.312(9) . ?
F5A C10A 1.320(7) . ?
F6A C10A 1.338(8) . ?
F7A C10A 1.340(8) . ?
O1A C4A 1.227(7) . ?
N1A N2A 1.348(6) . ?
N1A C3A 1.362(7) . ?
N2A C1A 1.336(8) . ?
C1A C2A 1.392(8) . ?
C1A C9A 1.489(8) . ?
C2A C3A 1.387(8) . ?
C3A C4A 1.479(8) . ?
C4A C5A 1.486(9) . ?
C5A C6A 1.509(8) . ?
C5A C8A 1.570(8) . ?
C6A C7A 1.533(8) . ?
C7A C8A 1.500(8) . ?
C9A C10A 1.512(9) . ?
C9A C11A 1.520(9) . ?
F1B C9B 1.366(7) . ?
F2B C11B 1.309(8) . ?
F3B C11B 1.361(8) . ?
F4B C11B 1.316(7) . ?
F5B C10B 1.337(7) . ?
F6B C10B 1.315(8) . ?
F7B C10B 1.290(8) . ?
O1B C4B 1.251(6) . ?
N1B N2B 1.309(7) . ?
N1B C3B 1.354(7) . ?
N2B C1B 1.329(7) . ?
C1B C2B 1.371(9) . ?
C1B C9B 1.530(9) . ?
C2B C3B 1.393(8) . ?
C3B C4B 1.459(9) . ?
C4B C5B 1.477(9) . ?
C5B C6B 1.510(10) . ?
C5B C8B 1.541(10) . ?
C6B C7B 1.572(10) . ?
C7B C8B 1.522(9) . ?
C9B C10B 1.535(8) . ?
C9B C11B 1.535(8) . ?
F1C C9C 1.385(7) . ?
F2C C11C 1.321(8) . ?
F3C C11C 1.348(7) . ?
F4C C11C 1.322(8) . ?
F5C C10C 1.325(7) . ?
F6C C10C 1.354(8) . ?
F7C C10C 1.340(8) . ?
O1C C4C 1.209(6) . ?
N1C C3C 1.336(7) . ?
N1C N2C 1.337(7) . ?
N2C C1C 1.309(7) . ?
C1C C2C 1.417(8) . ?
C1C C9C 1.512(8) . ?
C2C C3C 1.380(8) . ?
C3C C4C 1.518(8) . ?
C4C C5C 1.519(8) . ?
C5C C6C 1.521(10) . ?
C5C C8C 1.567(8) . ?
C6C C7C 1.557(9) . ?
C7C C8C 1.551(10) . ?
C9C C10C 1.506(10) . ?
C9C C11C 1.522(9) . ?
F1D C9D 1.392(7) . ?
F2D C11D 1.319(8) . ?
F3D C11D 1.306(8) . ?
F4D C11D 1.330(8) . ?
F5D C10D 1.291(7) . ?
F6D C10D 1.322(7) . ?
F7D C10D 1.326(8) . ?
O1D C4D 1.237(6) . ?
N1D N2D 1.336(7) . ?
N1D C3D 1.375(8) . ?
N2D C1D 1.330(7) . ?
C1D C2D 1.375(9) . ?
C1D C9D 1.499(9) . ?
C2D C3D 1.379(8) . ?
C3D C4D 1.474(8) . ?
C4D C5D 1.451(9) . ?
C5D C8D 1.540(9) . ?
C5D C6D 1.553(8) . ?
C6D C7D 1.519(9) . ?
C7D C8D 1.547(8) . ?
C9D C11D 1.535(10) . ?
C9D C10D 1.569(10) . ?
F1E C9E 1.389(6) . ?
F2E C11E 1.318(8) . ?
F3E C11E 1.328(7) . ?
F4E C11E 1.340(7) . ?
F5E C10E 1.322(8) . ?
F6E C10E 1.303(9) . ?
F7E C10E 1.316(8) . ?
O1E C4E 1.225(7) . ?
N1E N2E 1.339(6) . ?
N1E C3E 1.371(7) . ?
N2E C1E 1.316(7) . ?
C1E C2E 1.408(8) . ?
C1E C9E 1.499(9) . ?
C2E C3E 1.359(7) . ?
C3E C4E 1.493(8) . ?
C4E C5E 1.504(9) . ?
C5E C8E 1.533(7) . ?
C5E C6E 1.537(9) . ?
C6E C7E 1.563(9) . ?
C7E C8E 1.536(9) . ?
C9E C11E 1.524(10) . ?
C9E C10E 1.563(10) . ?
F1F C9F 1.401(7) . ?
F2F C11F 1.337(8) . ?
F3F C11F 1.307(7) . ?
F4F C11F 1.309(8) . ?
F5F C10F 1.304(8) . ?
F6F C10F 1.367(8) . ?
F7F C10F 1.335(8) . ?
O1F C4F 1.234(6) . ?
N1F N2F 1.353(7) . ?
N1F C3F 1.358(7) . ?
N2F C1F 1.323(7) . ?
C1F C2F 1.383(9) . ?
C1F C9F 1.504(9) . ?
C2F C3F 1.371(8) . ?
C3F C4F 1.445(9) . ?
C4F C5F 1.480(9) . ?
C5F C6F 1.528(8) . ?
C5F C8F 1.555(9) . ?
C6F C7F 1.535(9) . ?
C7F C8F 1.537(9) . ?
C9F C10F 1.510(10) . ?
C9F C11F 1.549(9) . ?

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
N2A N1A C3A 110.6(5) . . ?
C1A N2A N1A 105.8(5) . . ?
N2A C1A C2A 111.7(5) . . ?
N2A C1A C9A 124.0(6) . . ?
C2A C1A C9A 124.3(6) . . ?
C3A C2A C1A 104.2(5) . . ?
N1A C3A C2A 107.7(5) . . ?
N1A C3A C4A 120.5(5) . . ?
C2A C3A C4A 131.6(5) . . ?
O1A C4A C3A 119.1(5) . . ?
O1A C4A C5A 124.5(5) . . ?
C3A C4A C5A 116.3(5) . . ?
C4A C5A C6A 118.4(5) . . ?
C4A C5A C8A 118.8(6) . . ?
C6A C5A C8A 88.2(5) . . ?
C5A C6A C7A 88.7(4) . . ?
C8A C7A C6A 89.9(5) . . ?
C7A C8A C5A 87.7(5) . . ?
F1A C9A C1A 109.4(5) . . ?
F1A C9A C10A 104.5(5) . . ?
C1A C9A C10A 113.2(5) . . ?
F1A C9A C11A 106.0(5) . . ?
C1A C9A C11A 112.3(6) . . ?
C10A C9A C11A 111.0(5) . . ?
F5A C10A F6A 107.9(6) . . ?
F5A C10A F7A 107.9(6) . . ?
F6A C10A F7A 107.2(5) . . ?
F5A C10A C9A 113.6(5) . . ?
F6A C10A C9A 111.6(6) . . ?
F7A C10A C9A 108.3(6) . . ?
F4A C11A F3A 108.9(6) . . ?
F4A C11A F2A 105.4(7) . . ?
F3A C11A F2A 107.2(6) . . ?
F4A C11A C9A 113.8(6) . . ?
F3A C11A C9A 112.1(6) . . ?
F2A C11A C9A 109.0(6) . . ?
N2B N1B C3B 113.5(5) . . ?
N1B N2B C1B 105.1(5) . . ?
N2B C1B C2B 111.6(6) . . ?
N2B C1B C9B 118.3(6) . . ?
C2B C1B C9B 130.1(5) . . ?
C1B C2B C3B 105.2(5) . . ?
N1B C3B C2B 104.6(5) . . ?
N1B C3B C4B 121.5(5) . . ?
C2B C3B C4B 133.9(5) . . ?
O1B C4B C3B 117.8(5) . . ?
O1B C4B C5B 121.2(6) . . ?
C3B C4B C5B 120.7(5) . . ?
C4B C5B C6B 118.5(6) . . ?
C4B C5B C8B 119.4(6) . . ?
C6B C5B C8B 91.6(5) . . ?
C5B C6B C7B 86.3(5) . . ?
C8B C7B C6B 90.0(5) . . ?
C7B C8B C5B 86.9(5) . . ?
F1B C9B C1B 110.3(4) . . ?
F1B C9B C10B 107.2(5) . . ?
C1B C9B C10B 110.2(5) . . ?
F1B C9B C11B 105.8(5) . . ?
C1B C9B C11B 108.9(5) . . ?
C10B C9B C11B 114.3(5) . . ?
F7B C10B F6B 111.3(6) . . ?
F7B C10B F5B 107.8(6) . . ?
F6B C10B F5B 107.0(5) . . ?
F7B C10B C9B 109.4(5) . . ?
F6B C10B C9B 111.5(6) . . ?
F5B C10B C9B 109.9(5) . . ?
F2B C11B F4B 108.6(6) . . ?
F2B C11B F3B 106.0(5) . . ?
F4B C11B F3B 108.1(4) . . ?
F2B C11B C9B 111.7(5) . . ?
F4B C11B C9B 111.6(6) . . ?
F3B C11B C9B 110.6(6) . . ?
C3C N1C N2C 111.7(5) . . ?
C1C N2C N1C 105.3(5) . . ?
N2C C1C C2C 112.4(5) . . ?
N2C C1C C9C 119.8(6) . . ?
C2C C1C C9C 127.7(5) . . ?
C3C C2C C1C 102.2(5) . . ?
N1C C3C C2C 108.3(5) . . ?
N1C C3C C4C 118.8(5) . . ?
C2C C3C C4C 132.8(5) . . ?
O1C C4C C3C 118.5(5) . . ?
O1C C4C C5C 125.1(6) . . ?
C3C C4C C5C 116.3(5) . . ?
C4C C5C C6C 119.8(6) . . ?
C4C C5C C8C 114.6(5) . . ?
C6C C5C C8C 89.6(5) . . ?
C5C C6C C7C 88.4(5) . . ?
C8C C7C C6C 88.8(5) . . ?
C7C C8C C5C 87.0(5) . . ?
F1C C9C C10C 105.3(6) . . ?
F1C C9C C1C 109.0(5) . . ?
C10C C9C C1C 112.1(5) . . ?
F1C C9C C11C 104.8(5) . . ?
C10C C9C C11C 114.4(5) . . ?
C1C C9C C11C 110.7(6) . . ?
F5C C10C F7C 106.6(6) . . ?
F5C C10C F6C 106.9(5) . . ?
F7C C10C F6C 107.6(6) . . ?
F5C C10C C9C 113.2(6) . . ?
F7C C10C C9C 112.4(5) . . ?
F6C C10C C9C 109.8(6) . . ?
F2C C11C F4C 108.0(6) . . ?
F2C C11C F3C 108.4(6) . . ?
F4C C11C F3C 105.8(5) . . ?
F2C C11C C9C 110.9(5) . . ?
F4C C11C C9C 111.3(5) . . ?
F3C C11C C9C 112.1(6) . . ?
N2D N1D C3D 111.6(5) . . ?
C1D N2D N1D 105.5(5) . . ?
N2D C1D C2D 111.5(6) . . ?
N2D C1D C9D 121.1(6) . . ?
C2D C1D C9D 127.3(6) . . ?
C1D C2D C3D 105.9(5) . . ?
N1D C3D C2D 105.4(6) . . ?
N1D C3D C4D 121.8(5) . . ?
C2D C3D C4D 132.8(6) . . ?
O1D C4D C5D 124.2(6) . . ?
O1D C4D C3D 117.7(5) . . ?
C5D C4D C3D 118.1(5) . . ?
C4D C5D C8D 118.1(5) . . ?
C4D C5D C6D 120.2(5) . . ?
C8D C5D C6D 86.8(5) . . ?
C7D C6D C5D 89.8(5) . . ?
C6D C7D C8D 87.8(5) . . ?
C5D C8D C7D 89.2(5) . . ?
F1D C9D C1D 107.7(6) . . ?
F1D C9D C11D 107.0(5) . . ?
C1D C9D C11D 111.6(6) . . ?
F1D C9D C10D 104.2(5) . . ?
C1D C9D C10D 114.2(6) . . ?
C11D C9D C10D 111.5(6) . . ?
F5D C10D F6D 108.2(6) . . ?
F5D C10D F7D 108.4(5) . . ?
F6D C10D F7D 107.4(5) . . ?
F5D C10D C9D 111.6(5) . . ?
F6D C10D C9D 111.3(5) . . ?
F7D C10D C9D 109.8(6) . . ?
F3D C11D F2D 107.8(6) . . ?
F3D C11D F4D 109.8(6) . . ?
F2D C11D F4D 110.5(7) . . ?
F3D C11D C9D 112.8(6) . . ?
F2D C11D C9D 106.9(7) . . ?
F4D C11D C9D 109.1(5) . . ?
N2E N1E C3E 111.8(5) . . ?
C1E N2E N1E 104.6(5) . . ?
N2E C1E C2E 112.7(5) . . ?
N2E C1E C9E 123.2(6) . . ?
C2E C1E C9E 124.0(5) . . ?
C3E C2E C1E 103.9(5) . . ?
C2E C3E N1E 107.0(5) . . ?
C2E C3E C4E 132.3(5) . . ?
N1E C3E C4E 120.5(5) . . ?
O1E C4E C3E 119.5(6) . . ?
O1E C4E C5E 124.7(5) . . ?
C3E C4E C5E 115.8(5) . . ?
C4E C5E C8E 119.0(5) . . ?
C4E C5E C6E 118.2(6) . . ?
C8E C5E C6E 89.3(5) . . ?
C5E C6E C7E 87.2(5) . . ?
C8E C7E C6E 88.3(5) . . ?
C5E C8E C7E 88.3(4) . . ?
F1E C9E C1E 109.0(5) . . ?
F1E C9E C11E 104.5(5) . . ?
C1E C9E C11E 113.0(5) . . ?
F1E C9E C10E 106.3(4) . . ?
C1E C9E C10E 110.6(6) . . ?
C11E C9E C10E 113.0(6) . . ?
F6E C10E F7E 111.0(8) . . ?
F6E C10E F5E 108.4(6) . . ?
F7E C10E F5E 108.0(5) . . ?
F6E C10E C9E 111.0(5) . . ?
F7E C10E C9E 109.0(6) . . ?
F5E C10E C9E 109.3(7) . . ?
F2E C11E F3E 108.2(6) . . ?
F2E C11E F4E 109.5(5) . . ?
F3E C11E F4E 106.5(6) . . ?
F2E C11E C9E 109.9(6) . . ?
F3E C11E C9E 112.0(5) . . ?
F4E C11E C9E 110.7(6) . . ?
N2F N1F C3F 112.8(4) . . ?
C1F N2F N1F 103.8(5) . . ?
N2F C1F C2F 112.2(6) . . ?
N2F C1F C9F 122.9(6) . . ?
C2F C1F C9F 124.9(5) . . ?
C3F C2F C1F 105.8(5) . . ?
N1F C3F C2F 105.3(5) . . ?
N1F C3F C4F 121.7(5) . . ?
C2F C3F C4F 133.0(6) . . ?
O1F C4F C3F 120.8(6) . . ?
O1F C4F C5F 122.9(6) . . ?
C3F C4F C5F 116.3(5) . . ?
C4F C5F C6F 121.4(6) . . ?
C4F C5F C8F 119.4(5) . . ?
C6F C5F C8F 87.5(5) . . ?
C5F C6F C7F 89.2(5) . . ?
C6F C7F C8F 87.9(5) . . ?
C7F C8F C5F 88.1(5) . . ?
F1F C9F C1F 109.6(5) . . ?
F1F C9F C10F 104.3(5) . . ?
C1F C9F C10F 113.4(6) . . ?
F1F C9F C11F 105.0(5) . . ?
C1F C9F C11F 111.5(5) . . ?
C10F C9F C11F 112.4(6) . . ?
F5F C10F F7F 108.4(5) . . ?
F5F C10F F6F 108.7(7) . . ?
F7F C10F F6F 106.5(6) . . ?
F5F C10F C9F 113.3(6) . . ?
F7F C10F C9F 110.5(7) . . ?
F6F C10F C9F 109.1(6) . . ?
F3F C11F F4F 107.5(6) . . ?
F3F C11F F2F 107.9(6) . . ?
F4F C11F F2F 107.8(6) . . ?
F3F C11F C9F 113.3(5) . . ?
F4F C11F C9F 111.0(5) . . ?
F2F C11F C9F 109.0(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3A N1A N2A C1A 1.3(6) . . . . ?
N1A N2A C1A C2A -0.5(7) . . . . ?
N1A N2A C1A C9A 178.1(5) . . . . ?
N2A C1A C2A C3A -0.4(7) . . . . ?
C9A C1A C2A C3A -179.0(6) . . . . ?
N2A N1A C3A C2A -1.6(6) . . . . ?
N2A N1A C3A C4A -176.6(5) . . . . ?
C1A C2A C3A N1A 1.2(6) . . . . ?
C1A C2A C3A C4A 175.5(6) . . . . ?
N1A C3A C4A O1A -1.7(8) . . . . ?
C2A C3A C4A O1A -175.4(6) . . . . ?
N1A C3A C4A C5A 176.7(5) . . . . ?
C2A C3A C4A C5A 3.0(9) . . . . ?
O1A C4A C5A C6A -120.3(7) . . . . ?
C3A C4A C5A C6A 61.3(8) . . . . ?
O1A C4A C5A C8A -15.5(9) . . . . ?
C3A C4A C5A C8A 166.2(5) . . . . ?
C4A C5A C6A C7A 139.2(6) . . . . ?
C8A C5A C6A C7A 17.2(5) . . . . ?
C5A C6A C7A C8A -18.0(6) . . . . ?
C6A C7A C8A C5A 17.3(5) . . . . ?
C4A C5A C8A C7A -139.3(6) . . . . ?
C6A C5A C8A C7A -17.6(5) . . . . ?
N2A C1A C9A F1A -178.2(5) . . . . ?
C2A C1A C9A F1A 0.2(8) . . . . ?
N2A C1A C9A C10A -62.2(8) . . . . ?
C2A C1A C9A C10A 116.2(7) . . . . ?
N2A C1A C9A C11A 64.4(8) . . . . ?
C2A C1A C9A C11A -117.2(7) . . . . ?
F1A C9A C10A F5A -55.6(7) . . . . ?
C1A C9A C10A F5A -174.5(6) . . . . ?
C11A C9A C10A F5A 58.2(8) . . . . ?
F1A C9A C10A F6A -177.9(5) . . . . ?
C1A C9A C10A F6A 63.2(7) . . . . ?
C11A C9A C10A F6A -64.1(7) . . . . ?
F1A C9A C10A F7A 64.2(6) . . . . ?
C1A C9A C10A F7A -54.7(7) . . . . ?
C11A C9A C10A F7A 178.0(5) . . . . ?
F1A C9A C11A F4A 177.3(6) . . . . ?
C1A C9A C11A F4A -63.4(8) . . . . ?
C10A C9A C11A F4A 64.4(8) . . . . ?
F1A C9A C11A F3A 53.0(7) . . . . ?
C1A C9A C11A F3A 172.4(6) . . . . ?
C10A C9A C11A F3A -59.8(7) . . . . ?
F1A C9A C11A F2A -65.4(7) . . . . ?
C1A C9A C11A F2A 53.9(8) . . . . ?
C10A C9A C11A F2A -178.3(6) . . . . ?
C3B N1B N2B C1B -0.2(7) . . . . ?
N1B N2B C1B C2B 0.2(7) . . . . ?
N1B N2B C1B C9B 179.4(5) . . . . ?
N2B C1B C2B C3B -0.1(7) . . . . ?
C9B C1B C2B C3B -179.2(6) . . . . ?
N2B N1B C3B C2B 0.2(6) . . . . ?
N2B N1B C3B C4B 178.0(5) . . . . ?
C1B C2B C3B N1B 0.0(6) . . . . ?
C1B C2B C3B C4B -177.4(7) . . . . ?
N1B C3B C4B O1B -7.7(9) . . . . ?
C2B C3B C4B O1B 169.3(6) . . . . ?
N1B C3B C4B C5B 166.0(6) . . . . ?
C2B C3B C4B C5B -16.9(11) . . . . ?
O1B C4B C5B C6B -134.1(7) . . . . ?
C3B C4B C5B C6B 52.4(9) . . . . ?
O1B C4B C5B C8B -24.0(10) . . . . ?
C3B C4B C5B C8B 162.4(6) . . . . ?
C4B C5B C6B C7B 142.0(6) . . . . ?
C8B C5B C6B C7B 16.9(6) . . . . ?
C5B C6B C7B C8B -17.1(6) . . . . ?
C6B C7B C8B C5B 16.8(6) . . . . ?
C4B C5B C8B C7B -141.9(7) . . . . ?
C6B C5B C8B C7B -17.5(6) . . . . ?
N2B C1B C9B F1B 13.1(7) . . . . ?
C2B C1B C9B F1B -167.9(6) . . . . ?
N2B C1B C9B C10B 131.3(6) . . . . ?
C2B C1B C9B C10B -49.7(8) . . . . ?
N2B C1B C9B C11B -102.5(6) . . . . ?
C2B C1B C9B C11B 76.5(8) . . . . ?
F1B C9B C10B F7B 59.0(7) . . . . ?
C1B C9B C10B F7B -61.1(7) . . . . ?
C11B C9B C10B F7B 175.8(6) . . . . ?
F1B C9B C10B F6B -177.5(5) . . . . ?
C1B C9B C10B F6B 62.4(7) . . . . ?
C11B C9B C10B F6B -60.7(7) . . . . ?
F1B C9B C10B F5B -59.1(7) . . . . ?
C1B C9B C10B F5B -179.2(5) . . . . ?
C11B C9B C10B F5B 57.7(8) . . . . ?
F1B C9B C11B F2B -64.8(7) . . . . ?
C1B C9B C11B F2B 53.8(7) . . . . ?
C10B C9B C11B F2B 177.6(5) . . . . ?
F1B C9B C11B F4B 173.4(5) . . . . ?
C1B C9B C11B F4B -68.1(6) . . . . ?
C10B C9B C11B F4B 55.7(8) . . . . ?
F1B C9B C11B F3B 53.0(6) . . . . ?
C1B C9B C11B F3B 171.6(5) . . . . ?
C10B C9B C11B F3B -64.6(7) . . . . ?
C3C N1C N2C C1C 0.6(7) . . . . ?
N1C N2C C1C C2C 0.4(7) . . . . ?
N1C N2C C1C C9C 177.5(6) . . . . ?
N2C C1C C2C C3C -1.3(7) . . . . ?
C9C C1C C2C C3C -178.1(6) . . . . ?
N2C N1C C3C C2C -1.5(7) . . . . ?
N2C N1C C3C C4C 177.7(5) . . . . ?
C1C C2C C3C N1C 1.6(6) . . . . ?
C1C C2C C3C C4C -177.4(6) . . . . ?
N1C C3C C4C O1C -8.1(8) . . . . ?
C2C C3C C4C O1C 170.8(6) . . . . ?
N1C C3C C4C C5C 170.2(5) . . . . ?
C2C C3C C4C C5C -10.9(10) . . . . ?
O1C C4C C5C C6C -121.2(7) . . . . ?
C3C C4C C5C C6C 60.6(7) . . . . ?
O1C C4C C5C C8C -16.5(9) . . . . ?
C3C C4C C5C C8C 165.3(5) . . . . ?
C4C C5C C6C C7C 137.0(5) . . . . ?
C8C C5C C6C C7C 18.5(5) . . . . ?
C5C C6C C7C C8C -18.7(5) . . . . ?
C6C C7C C8C C5C 18.2(5) . . . . ?
C4C C5C C8C C7C -141.6(6) . . . . ?
C6C C5C C8C C7C -18.6(5) . . . . ?
N2C C1C C9C F1C 15.7(8) . . . . ?
C2C C1C C9C F1C -167.7(6) . . . . ?
N2C C1C C9C C10C 131.9(6) . . . . ?
C2C C1C C9C C10C -51.5(9) . . . . ?
N2C C1C C9C C11C -99.0(7) . . . . ?
C2C C1C C9C C11C 77.6(8) . . . . ?
F1C C9C C10C F5C -55.7(7) . . . . ?
C1C C9C C10C F5C -174.2(5) . . . . ?
C11C C9C C10C F5C 58.8(8) . . . . ?
F1C C9C C10C F7C 65.2(6) . . . . ?
C1C C9C C10C F7C -53.2(8) . . . . ?
C11C C9C C10C F7C 179.7(5) . . . . ?
F1C C9C C10C F6C -175.1(4) . . . . ?
C1C C9C C10C F6C 66.5(7) . . . . ?
C11C C9C C10C F6C -60.6(7) . . . . ?
F1C C9C C11C F2C -59.4(7) . . . . ?
C10C C9C C11C F2C -174.3(5) . . . . ?
C1C C9C C11C F2C 57.9(8) . . . . ?
F1C C9C C11C F4C -179.7(5) . . . . ?
C10C C9C C11C F4C 65.4(7) . . . . ?
C1C C9C C11C F4C -62.4(7) . . . . ?
F1C C9C C11C F3C 61.9(7) . . . . ?
C10C C9C C11C F3C -52.9(8) . . . . ?
C1C C9C C11C F3C 179.2(6) . . . . ?
C3D N1D N2D C1D 0.7(7) . . . . ?
N1D N2D C1D C2D -1.5(7) . . . . ?
N1D N2D C1D C9D -179.1(6) . . . . ?
N2D C1D C2D C3D 1.7(7) . . . . ?
C9D C1D C2D C3D 179.1(6) . . . . ?
N2D N1D C3D C2D 0.3(6) . . . . ?
N2D N1D C3D C4D 177.5(5) . . . . ?
C1D C2D C3D N1D -1.1(6) . . . . ?
C1D C2D C3D C4D -177.9(6) . . . . ?
N1D C3D C4D O1D -0.8(9) . . . . ?
C2D C3D C4D O1D 175.5(6) . . . . ?
N1D C3D C4D C5D -179.4(5) . . . . ?
C2D C3D C4D C5D -3.1(10) . . . . ?
O1D C4D C5D C8D 17.8(9) . . . . ?
C3D C4D C5D C8D -163.8(6) . . . . ?
O1D C4D C5D C6D 121.5(7) . . . . ?
C3D C4D C5D C6D -60.1(8) . . . . ?
C4D C5D C6D C7D -139.9(6) . . . . ?
C8D C5D C6D C7D -19.0(5) . . . . ?
C5D C6D C7D C8D 18.9(5) . . . . ?
C4D C5D C8D C7D 141.5(6) . . . . ?
C6D C5D C8D C7D 18.7(5) . . . . ?
C6D C7D C8D C5D -19.1(5) . . . . ?
N2D C1D C9D F1D -154.7(6) . . . . ?
C2D C1D C9D F1D 28.1(9) . . . . ?
N2D C1D C9D C11D 88.1(8) . . . . ?
C2D C1D C9D C11D -89.1(8) . . . . ?
N2D C1D C9D C10D -39.5(9) . . . . ?
C2D C1D C9D C10D 143.3(7) . . . . ?
F1D C9D C10D F5D -55.5(7) . . . . ?
C1D C9D C10D F5D -172.8(5) . . . . ?
C11D C9D C10D F5D 59.5(7) . . . . ?
F1D C9D C10D F6D -176.5(5) . . . . ?
C1D C9D C10D F6D 66.2(8) . . . . ?
C11D C9D C10D F6D -61.5(7) . . . . ?
F1D C9D C10D F7D 64.7(6) . . . . ?
C1D C9D C10D F7D -52.5(7) . . . . ?
C11D C9D C10D F7D 179.8(5) . . . . ?
F1D C9D C11D F3D 55.3(8) . . . . ?
C1D C9D C11D F3D 172.9(6) . . . . ?
C10D C9D C11D F3D -58.0(8) . . . . ?
F1D C9D C11D F2D -62.9(7) . . . . ?
C1D C9D C11D F2D 54.7(8) . . . . ?
C10D C9D C11D F2D -176.2(6) . . . . ?
F1D C9D C11D F4D 177.6(6) . . . . ?
C1D C9D C11D F4D -64.8(8) . . . . ?
C10D C9D C11D F4D 64.3(7) . . . . ?
C3E N1E N2E C1E 0.2(6) . . . . ?
N1E N2E C1E C2E -0.7(7) . . . . ?
N1E N2E C1E C9E -176.0(5) . . . . ?
N2E C1E C2E C3E 0.9(7) . . . . ?
C9E C1E C2E C3E 176.2(6) . . . . ?
C1E C2E C3E N1E -0.7(6) . . . . ?
C1E C2E C3E C4E -176.1(6) . . . . ?
N2E N1E C3E C2E 0.4(6) . . . . ?
N2E N1E C3E C4E 176.4(5) . . . . ?
C2E C3E C4E O1E 168.1(6) . . . . ?
N1E C3E C4E O1E -6.8(9) . . . . ?
C2E C3E C4E C5E -13.2(10) . . . . ?
N1E C3E C4E C5E 172.0(5) . . . . ?
O1E C4E C5E C8E -13.2(9) . . . . ?
C3E C4E C5E C8E 168.2(6) . . . . ?
O1E C4E C5E C6E -119.6(7) . . . . ?
C3E C4E C5E C6E 61.8(7) . . . . ?
C4E C5E C6E C7E 142.6(5) . . . . ?
C8E C5E C6E C7E 19.7(5) . . . . ?
C5E C6E C7E C8E -19.6(5) . . . . ?
C4E C5E C8E C7E -142.3(6) . . . . ?
C6E C5E C8E C7E -20.0(5) . . . . ?
C6E C7E C8E C5E 19.7(5) . . . . ?
N2E C1E C9E F1E -178.7(6) . . . . ?
C2E C1E C9E F1E 6.5(8) . . . . ?
N2E C1E C9E C11E 65.6(8) . . . . ?
C2E C1E C9E C11E -109.2(7) . . . . ?
N2E C1E C9E C10E -62.3(8) . . . . ?
C2E C1E C9E C10E 123.0(7) . . . . ?
F1E C9E C10E F6E -173.0(6) . . . . ?
C1E C9E C10E F6E 68.8(8) . . . . ?
C11E C9E C10E F6E -59.1(8) . . . . ?
F1E C9E C10E F7E 64.4(8) . . . . ?
C1E C9E C10E F7E -53.8(7) . . . . ?
C11E C9E C10E F7E 178.4(5) . . . . ?
F1E C9E C10E F5E -53.5(7) . . . . ?
C1E C9E C10E F5E -171.7(5) . . . . ?
C11E C9E C10E F5E 60.5(7) . . . . ?
F1E C9E C11E F2E -62.4(6) . . . . ?
C1E C9E C11E F2E 56.0(7) . . . . ?
C10E C9E C11E F2E -177.5(5) . . . . ?
F1E C9E C11E F3E 57.8(7) . . . . ?
C1E C9E C11E F3E 176.2(5) . . . . ?
C10E C9E C11E F3E -57.3(7) . . . . ?
F1E C9E C11E F4E 176.5(5) . . . . ?
C1E C9E C11E F4E -65.1(7) . . . . ?
C10E C9E C11E F4E 61.4(7) . . . . ?
C3F N1F N2F C1F 0.1(6) . . . . ?
N1F N2F C1F C2F -0.7(7) . . . . ?
N1F N2F C1F C9F 179.0(5) . . . . ?
N2F C1F C2F C3F 1.0(7) . . . . ?
C9F C1F C2F C3F -178.7(6) . . . . ?
N2F N1F C3F C2F 0.5(6) . . . . ?
N2F N1F C3F C4F -178.2(5) . . . . ?
C1F C2F C3F N1F -0.8(7) . . . . ?
C1F C2F C3F C4F 177.7(6) . . . . ?
N1F C3F C4F O1F 7.3(9) . . . . ?
C2F C3F C4F O1F -171.0(6) . . . . ?
N1F C3F C4F C5F -172.2(5) . . . . ?
C2F C3F C4F C5F 9.5(10) . . . . ?
O1F C4F C5F C6F 123.0(7) . . . . ?
C3F C4F C5F C6F -57.5(8) . . . . ?
O1F C4F C5F C8F 16.4(9) . . . . ?
C3F C4F C5F C8F -164.2(5) . . . . ?
C4F C5F C6F C7F -143.6(6) . . . . ?
C8F C5F C6F C7F -20.2(5) . . . . ?
C5F C6F C7F C8F 20.4(5) . . . . ?
C6F C7F C8F C5F -20.1(5) . . . . ?
C4F C5F C8F C7F 145.3(6) . . . . ?
C6F C5F C8F C7F 20.2(5) . . . . ?
N2F C1F C9F F1F 172.8(5) . . . . ?
C2F C1F C9F F1F -7.6(9) . . . . ?
N2F C1F C9F C10F 56.7(8) . . . . ?
C2F C1F C9F C10F -123.6(7) . . . . ?
N2F C1F C9F C11F -71.4(8) . . . . ?
C2F C1F C9F C11F 108.3(7) . . . . ?
F1F C9F C10F F5F 56.2(8) . . . . ?
C1F C9F C10F F5F 175.4(6) . . . . ?
C11F C9F C10F F5F -56.9(8) . . . . ?
F1F C9F C10F F7F -65.6(7) . . . . ?
C1F C9F C10F F7F 53.6(8) . . . . ?
C11F C9F C10F F7F -178.8(5) . . . . ?
F1F C9F C10F F6F 177.5(6) . . . . ?
C1F C9F C10F F6F -63.3(8) . . . . ?
C11F C9F C10F F6F 64.4(8) . . . . ?
F1F C9F C11F F3F -53.9(7) . . . . ?
C1F C9F C11F F3F -172.5(5) . . . . ?
C10F C9F C11F F3F 58.8(8) . . . . ?
F1F C9F C11F F4F -175.1(5) . . . . ?
C1F C9F C11F F4F 66.3(7) . . . . ?
C10F C9F C11F F4F -62.3(8) . . . . ?
F1F C9F C11F F2F 66.3(6) . . . . ?
C1F C9F C11F F2F -52.4(7) . . . . ?
C10F C9F C11F F2F 179.0(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1NA O1F 0.88 2.04 2.893(6) 161.8 .
N1B H1NB O1A 0.88 2.00 2.820(6) 154.3 2_665
N1C H1NC O1D 0.88 2.03 2.848(7) 153.2 .
N1D H1ND O1E 0.88 2.02 2.866(6) 159.5 .
N1E H1NE O1B 0.88 2.02 2.834(6) 153.1 .
N1F H1NF O1C 0.88 2.02 2.826(6) 152.7 2_666

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.964
_refine_diff_density_max         1.014
_refine_diff_density_min         -0.601
_refine_diff_density_rms         0.136
####################################################################### 
# 
# 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_tolm325
_database_code_depnum_ccdc_archive 'CCDC 1541692'
_audit_update_record             
;
2017-06-23 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H8 F7 N3 O'
_chemical_formula_weight         307.18

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      tetragonal
_space_group_IT_number           78
_space_group_name_H-M_alt        'P 43'
_space_group_name_Hall           'P 4cw'

_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'
'-y, x, z+3/4'
'-x, -y, z+1/2'
'y, -x, z+1/4'

_cell_length_a                   14.9885(2)
_cell_length_b                   14.9885(2)
_cell_length_c                   20.7329(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4657.8(2)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.752
_exptl_crystal_F_000             2464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.994
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34628
_diffrn_reflns_av_unetI/netI     0.1035
_diffrn_reflns_av_R_equivalents  0.0883
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.039
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             13240
_reflns_number_gt                8218
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_max     0.952
_reflns_Friedel_fraction_full    0.962

_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)+(0.0764P)²] 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_abs_structure_details 
;
 Flack x determined using 2362 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         13240
_refine_ls_number_parameters     745
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1194
_refine_ls_R_factor_gt           0.0739
_refine_ls_wR_factor_ref         0.1880
_refine_ls_wR_factor_gt          0.1619
_refine_ls_goodness_of_fit_ref   0.986
_refine_ls_restrained_S_all      0.986
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1A F 0.8758(3) 0.5894(2) 0.73815(17) 0.0411(9) Uani 1 1 d . . . . .
F2A F 1.0431(3) 0.5564(3) 0.7023(2) 0.0511(11) Uani 1 1 d . . . . .
F3A F 1.0139(2) 0.6958(2) 0.7006(2) 0.0430(9) Uani 1 1 d . . . . .
F4A F 1.0265(3) 0.6235(3) 0.6118(2) 0.0500(10) Uani 1 1 d . . . . .
F5A F 0.8456(3) 0.7422(2) 0.6807(2) 0.0491(11) Uani 1 1 d . . . . .
F6A F 0.8598(3) 0.6876(2) 0.5853(2) 0.0544(12) Uani 1 1 d . . . . .
F7A F 0.7525(2) 0.6434(3) 0.6475(3) 0.0576(12) Uani 1 1 d . . . . .
O1A O 0.8206(3) 0.2353(3) 0.5698(2) 0.0409(10) Uani 1 1 d . . . . .
N1A N 0.8444(3) 0.4099(3) 0.5734(3) 0.0304(10) Uani 1 1 d . . . . .
H1NA H 0.825(5) 0.398(4) 0.536(4) 0.039(19) Uiso 1 1 d . . . . .
N2A N 0.8525(3) 0.4973(3) 0.5817(2) 0.0307(10) Uani 1 1 d . . . . .
N3A N 0.8705(3) 0.2097(3) 0.6706(3) 0.0317(11) Uani 1 1 d . . . . .
C1A C 0.8797(4) 0.5054(3) 0.6434(3) 0.0280(11) Uani 1 1 d . . . . .
C2A C 0.8893(4) 0.4228(3) 0.6741(3) 0.0274(11) Uani 1 1 d . . . . .
H2A H 0.9081 0.4111 0.7170 0.033 Uiso 1 1 calc R U . . .
C3A C 0.8647(3) 0.3616(4) 0.6264(3) 0.0255(11) Uani 1 1 d . . . . .
C4A C 0.8518(3) 0.2645(4) 0.6205(3) 0.0266(11) Uani 1 1 d . . . . .
C5A C 0.9108(6) 0.2380(4) 0.7311(4) 0.058(2) Uani 1 1 d . . . . .
H5AA H 0.9552 0.2845 0.7225 0.087 Uiso 1 1 calc R U . . .
H5AB H 0.9398 0.1869 0.7517 0.087 Uiso 1 1 calc R U . . .
H5AC H 0.8644 0.2617 0.7597 0.087 Uiso 1 1 calc R U . . .
C6A C 0.8503(5) 0.1143(4) 0.6652(4) 0.0436(16) Uani 1 1 d . . . . .
H6AA H 0.8263 0.1016 0.6222 0.065 Uiso 1 1 calc R U . . .
H6AB H 0.8061 0.0978 0.6979 0.065 Uiso 1 1 calc R U . . .
H6AC H 0.9050 0.0797 0.6719 0.065 Uiso 1 1 calc R U . . .
C7A C 0.8971(4) 0.5941(4) 0.6740(3) 0.0280(11) Uani 1 1 d . . . . .
C8A C 0.8376(4) 0.6686(4) 0.6456(4) 0.0388(15) Uani 1 1 d . . . . .
C9A C 0.9963(4) 0.6181(4) 0.6716(3) 0.0329(13) Uani 1 1 d . . . . .
F1B F 0.5547(4) -0.0487(3) 0.7382(2) 0.0651(14) Uani 1 1 d . . . . .
F2B F 0.7301(4) -0.0537(4) 0.7226(4) 0.120(3) Uani 1 1 d . . . . .
F3B F 0.6711(3) -0.1842(3) 0.7236(2) 0.0543(12) Uani 1 1 d . . . . .
F4B F 0.7191(4) -0.1264(5) 0.6366(3) 0.114(3) Uani 1 1 d . . . . .
F5B F 0.5049(3) -0.1968(2) 0.6816(2) 0.0533(11) Uani 1 1 d . . . . .
F6B F 0.5549(5) -0.1509(3) 0.5873(3) 0.099(2) Uani 1 1 d . . . . .
F7B F 0.4469(3) -0.0848(3) 0.6357(4) 0.119(3) Uani 1 1 d . . . . .
O1B O 0.5890(3) 0.2902(3) 0.5574(2) 0.0373(10) Uani 1 1 d . . . . .
N1B N 0.6256(3) 0.1146(3) 0.5698(2) 0.0276(10) Uani 1 1 d . . . . .
H1NB H 0.642(4) 0.129(4) 0.524(4) 0.043(19) Uiso 1 1 d . . . . .
N2B N 0.6211(3) 0.0276(3) 0.5818(3) 0.0312(10) Uani 1 1 d . . . . .
N3B N 0.6304(3) 0.3190(3) 0.6600(2) 0.0264(9) Uani 1 1 d . . . . .
C1B C 0.5996(3) 0.0231(3) 0.6446(3) 0.0256(11) Uani 1 1 d . . . . .
C2B C 0.5913(3) 0.1076(3) 0.6726(3) 0.0263(11) Uani 1 1 d . . . . .
H2B H 0.5768 0.1219 0.7160 0.032 Uiso 1 1 calc R U . . .
C3B C 0.6095(3) 0.1656(3) 0.6221(3) 0.0261(11) Uani 1 1 d . . . . .
C4B C 0.6095(3) 0.2630(3) 0.6111(3) 0.0248(10) Uani 1 1 d . . . . .
C5B C 0.6521(4) 0.2905(4) 0.7251(3) 0.0351(13) Uani 1 1 d . . . . .
H5BA H 0.6818 0.2323 0.7236 0.053 Uiso 1 1 calc R U . . .
H5BB H 0.5971 0.2856 0.7505 0.053 Uiso 1 1 calc R U . . .
H5BC H 0.6919 0.3343 0.7452 0.053 Uiso 1 1 calc R U . . .
C6B C 0.6267(4) 0.4141(3) 0.6483(3) 0.0332(13) Uani 1 1 d . . . . .
H6BA H 0.6300 0.4254 0.6018 0.050 Uiso 1 1 calc R U . . .
H6BB H 0.6771 0.4433 0.6698 0.050 Uiso 1 1 calc R U . . .
H6BC H 0.5706 0.4381 0.6653 0.050 Uiso 1 1 calc R U . . .
C7B C 0.5891(4) -0.0639(3) 0.6782(3) 0.0280(11) Uani 1 1 d . . . . .
C8B C 0.5201(5) -0.1239(4) 0.6459(5) 0.052(2) Uani 1 1 d . . . . .
C9B C 0.6774(5) -0.1104(5) 0.6893(4) 0.057(2) Uani 1 1 d . . . . .
F1C F 1.1230(3) 0.0980(3) 0.4367(2) 0.0569(12) Uani 1 1 d . . . . .
F2C F 1.0912(3) 0.2437(2) 0.3657(3) 0.0662(14) Uani 1 1 d . . . . .
F3C F 1.1923(3) 0.1585(3) 0.3285(3) 0.0627(13) Uani 1 1 d . . . . .
F4C F 1.0605(3) 0.1574(4) 0.2810(2) 0.0743(15) Uani 1 1 d . . . . .
F5C F 1.1695(2) -0.0127(2) 0.3333(2) 0.0468(10) Uani 1 1 d . . . . .
F6C F 1.0322(3) -0.0212(3) 0.3050(2) 0.0589(13) Uani 1 1 d . . . . .
F7C F 1.0710(3) -0.0598(3) 0.3998(2) 0.0573(12) Uani 1 1 d . . . . .
O1C O 0.6916(3) 0.1573(3) 0.4482(2) 0.0429(11) Uani 1 1 d . . . . .
N1C N 0.8671(3) 0.1522(3) 0.4538(3) 0.0299(10) Uani 1 1 d . . . . .
H1NC H 0.830(4) 0.180(4) 0.486(3) 0.039(18) Uiso 1 1 d . . . . .
N2C N 0.9547(3) 0.1418(3) 0.4541(3) 0.0378(12) Uani 1 1 d . . . . .
N3C N 0.6820(3) 0.1255(3) 0.3431(2) 0.0321(11) Uani 1 1 d . . . . .
C1C C 0.9718(4) 0.1081(4) 0.3963(4) 0.0373(14) Uani 1 1 d . . . . .
C2C C 0.8944(4) 0.0961(4) 0.3588(3) 0.0339(13) Uani 1 1 d . . . . .
H2C H 0.8897 0.0722 0.3165 0.041 Uiso 1 1 calc R U . . .
C3C C 0.8265(4) 0.1276(4) 0.3983(3) 0.0278(11) Uani 1 1 d . . . . .
C4C C 0.7279(3) 0.1359(3) 0.3971(3) 0.0262(11) Uani 1 1 d . . . . .
C5C C 0.7214(5) 0.1017(9) 0.2806(4) 0.086(4) Uani 1 1 d . . . . .
H5CA H 0.7718 0.1413 0.2714 0.128 Uiso 1 1 calc R U . . .
H5CB H 0.6763 0.1081 0.2466 0.128 Uiso 1 1 calc R U . . .
H5CC H 0.7422 0.0397 0.2819 0.128 Uiso 1 1 calc R U . . .
C6C C 0.5857(4) 0.1331(5) 0.3447(3) 0.0402(15) Uani 1 1 d . . . . .
H6CA H 0.5670 0.1563 0.3868 0.060 Uiso 1 1 calc R U . . .
H6CB H 0.5590 0.0742 0.3378 0.060 Uiso 1 1 calc R U . . .
H6CC H 0.5659 0.1739 0.3107 0.060 Uiso 1 1 calc R U . . .
C7C C 1.0689(4) 0.0920(4) 0.3801(4) 0.0420(16) Uani 1 1 d . . . . .
C8C C 1.1044(5) 0.1654(5) 0.3380(5) 0.054(2) Uani 1 1 d . . . . .
C9C C 1.0859(4) -0.0014(4) 0.3535(4) 0.0375(14) Uani 1 1 d . . . . .
F1D F 0.4271(2) 0.3627(3) 0.26125(17) 0.0394(8) Uani 1 1 d . . . . .
F2D F 0.4524(2) 0.5336(2) 0.2903(2) 0.0435(9) Uani 1 1 d . . . . .
F3D F 0.3126(2) 0.4990(2) 0.29116(19) 0.0382(9) Uani 1 1 d . . . . .
F4D F 0.3819(2) 0.5228(2) 0.38013(19) 0.0419(9) Uani 1 1 d . . . . .
F5D F 0.2718(2) 0.3308(2) 0.3138(2) 0.0443(10) Uani 1 1 d . . . . .
F6D F 0.3166(2) 0.3566(3) 0.41029(19) 0.0412(9) Uani 1 1 d . . . . .
F7D F 0.3701(2) 0.2460(2) 0.3570(2) 0.0437(10) Uani 1 1 d . . . . .
O1D O 0.7686(3) 0.3862(4) 0.4534(2) 0.0458(12) Uani 1 1 d . . . . .
N1D N 0.5926(3) 0.3534(3) 0.4353(2) 0.0277(10) Uani 1 1 d . . . . .
H1ND H 0.616(4) 0.338(4) 0.472(4) 0.034(18) Uiso 1 1 d . . . . .
N2D N 0.5063(3) 0.3558(3) 0.4206(2) 0.0299(10) Uani 1 1 d . . . . .
N3D N 0.8006(3) 0.3637(3) 0.3483(2) 0.0276(10) Uani 1 1 d . . . . .
C1D C 0.5040(3) 0.3782(3) 0.3592(3) 0.0228(10) Uani 1 1 d . . . . .
C2D C 0.5888(3) 0.3915(3) 0.3336(3) 0.0252(10) Uani 1 1 d . . . . .
H2D H 0.6040 0.4090 0.2910 0.030 Uiso 1 1 calc R U . . .
C3D C 0.6460(3) 0.3735(3) 0.3843(3) 0.0246(10) Uani 1 1 d . . . . .
C4D C 0.7440(3) 0.3755(4) 0.3969(3) 0.0273(11) Uani 1 1 d . . . . .
C5D C 0.7745(4) 0.3514(5) 0.2813(3) 0.0405(15) Uani 1 1 d . . . . .
H5DA H 0.7199 0.3155 0.2794 0.061 Uiso 1 1 calc R U . . .
H5DB H 0.8223 0.3207 0.2579 0.061 Uiso 1 1 calc R U . . .
H5DC H 0.7636 0.4097 0.2614 0.061 Uiso 1 1 calc R U . . .
C6D C 0.8959(4) 0.3673(4) 0.3601(3) 0.0378(14) Uani 1 1 d . . . . .
H6DA H 0.9067 0.3771 0.4061 0.057 Uiso 1 1 calc R U . . .
H6DB H 0.9220 0.4164 0.3352 0.057 Uiso 1 1 calc R U . . .
H6DC H 0.9233 0.3108 0.3468 0.057 Uiso 1 1 calc R U . . .
C7D C 0.4168(3) 0.3894(4) 0.3250(3) 0.0244(10) Uani 1 1 d . . . . .
C8D C 0.3424(4) 0.3295(4) 0.3524(3) 0.0337(13) Uani 1 1 d . . . . .
C9D C 0.3894(3) 0.4874(4) 0.3220(3) 0.0290(12) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1A C7A 1.369(7) . ?
F2A C9A 1.323(7) . ?
F3A C9A 1.338(6) . ?
F4A C9A 1.322(8) . ?
F5A C8A 1.327(7) . ?
F6A C8A 1.325(9) . ?
F7A C8A 1.330(7) . ?
O1A C4A 1.231(7) . ?
N1A N2A 1.327(6) . ?
N1A C3A 1.351(7) . ?
N1A H1NA 0.84(8) . ?
N2A C1A 1.349(8) . ?
N3A C4A 1.352(7) . ?
N3A C5A 1.455(9) . ?
N3A C6A 1.466(7) . ?
C1A C2A 1.399(8) . ?
C1A C7A 1.497(7) . ?
C2A C3A 1.397(7) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.473(8) . ?
C5A H5AA 0.9800 . ?
C5A H5AB 0.9800 . ?
C5A H5AC 0.9800 . ?
C6A H6AA 0.9800 . ?
C6A H6AB 0.9800 . ?
C6A H6AC 0.9800 . ?
C7A C9A 1.531(8) . ?
C7A C8A 1.546(8) . ?
F1B C7B 1.365(7) . ?
F2B C9B 1.350(11) . ?
F3B C9B 1.318(8) . ?
F4B C9B 1.282(10) . ?
F5B C8B 1.339(8) . ?
F6B C8B 1.384(11) . ?
F7B C8B 1.262(8) . ?
O1B C4B 1.226(7) . ?
N1B N2B 1.330(6) . ?
N1B C3B 1.348(7) . ?
N1B H1NB 1.00(8) . ?
N2B C1B 1.345(7) . ?
N3B C4B 1.353(7) . ?
N3B C6B 1.447(7) . ?
N3B C5B 1.453(8) . ?
C1B C2B 1.399(8) . ?
C1B C7B 1.487(7) . ?
C2B C3B 1.389(8) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.477(7) . ?
C5B H5BA 0.9800 . ?
C5B H5BB 0.9800 . ?
C5B H5BC 0.9800 . ?
C6B H6BA 0.9800 . ?
C6B H6BB 0.9800 . ?
C6B H6BC 0.9800 . ?
C7B C9B 1.514(9) . ?
C7B C8B 1.525(9) . ?
F1C C7C 1.431(8) . ?
F2C C8C 1.320(8) . ?
F3C C8C 1.336(7) . ?
F4C C8C 1.359(10) . ?
F5C C9C 1.332(7) . ?
F6C C9C 1.322(7) . ?
F7C C9C 1.319(8) . ?
O1C C4C 1.234(7) . ?
N1C N2C 1.322(6) . ?
N1C C3C 1.353(7) . ?
N1C H1NC 0.97(7) . ?
N2C C1C 1.326(9) . ?
N3C C4C 1.323(7) . ?
N3C C6C 1.449(7) . ?
N3C C5C 1.468(9) . ?
C1C C2C 1.408(9) . ?
C1C C7C 1.513(8) . ?
C2C C3C 1.389(8) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.483(7) . ?
C5C H5CA 0.9800 . ?
C5C H5CB 0.9800 . ?
C5C H5CC 0.9800 . ?
C6C H6CA 0.9800 . ?
C6C H6CB 0.9800 . ?
C6C H6CC 0.9800 . ?
C7C C8C 1.502(10) . ?
C7C C9C 1.525(9) . ?
F1D C7D 1.390(7) . ?
F2D C9D 1.343(6) . ?
F3D C9D 1.329(6) . ?
F4D C9D 1.321(7) . ?
F5D C8D 1.327(7) . ?
F6D C8D 1.324(8) . ?
F7D C8D 1.322(6) . ?
O1D C4D 1.240(7) . ?
N1D N2D 1.330(6) . ?
N1D C3D 1.359(7) . ?
N1D H1ND 0.88(7) . ?
N2D C1D 1.318(7) . ?
N3D C4D 1.330(7) . ?
N3D C6D 1.449(7) . ?
N3D C5D 1.455(8) . ?
C1D C2D 1.391(7) . ?
C1D C7D 1.497(7) . ?
C2D C3D 1.382(7) . ?
C2D H2D 0.9500 . ?
C3D C4D 1.492(7) . ?
C5D H5DA 0.9800 . ?
C5D H5DB 0.9800 . ?
C5D H5DC 0.9800 . ?
C6D H6DA 0.9800 . ?
C6D H6DB 0.9800 . ?
C6D H6DC 0.9800 . ?
C7D C9D 1.527(8) . ?
C7D C8D 1.540(8) . ?

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
N2A N1A C3A 113.8(5) . . ?
N2A N1A H1NA 111(5) . . ?
C3A N1A H1NA 135(5) . . ?
N1A N2A C1A 103.8(5) . . ?
C4A N3A C5A 124.8(5) . . ?
C4A N3A C6A 119.4(5) . . ?
C5A N3A C6A 115.8(5) . . ?
N2A C1A C2A 112.5(5) . . ?
N2A C1A C7A 122.3(5) . . ?
C2A C1A C7A 125.2(5) . . ?
C3A C2A C1A 103.5(5) . . ?
C3A C2A H2A 128.3 . . ?
C1A C2A H2A 128.3 . . ?
N1A C3A C2A 106.4(5) . . ?
N1A C3A C4A 115.6(5) . . ?
C2A C3A C4A 137.9(5) . . ?
O1A C4A N3A 121.2(5) . . ?
O1A C4A C3A 118.2(5) . . ?
N3A C4A C3A 120.6(5) . . ?
N3A C5A H5AA 109.5 . . ?
N3A C5A H5AB 109.5 . . ?
H5AA C5A H5AB 109.5 . . ?
N3A C5A H5AC 109.5 . . ?
H5AA C5A H5AC 109.5 . . ?
H5AB C5A H5AC 109.5 . . ?
N3A C6A H6AA 109.5 . . ?
N3A C6A H6AB 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
N3A C6A H6AC 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
F1A C7A C1A 109.0(5) . . ?
F1A C7A C9A 105.8(5) . . ?
C1A C7A C9A 111.3(5) . . ?
F1A C7A C8A 105.8(5) . . ?
C1A C7A C8A 112.3(5) . . ?
C9A C7A C8A 112.2(5) . . ?
F6A C8A F5A 108.4(5) . . ?
F6A C8A F7A 109.2(6) . . ?
F5A C8A F7A 107.9(5) . . ?
F6A C8A C7A 111.7(5) . . ?
F5A C8A C7A 109.8(5) . . ?
F7A C8A C7A 109.7(5) . . ?
F4A C9A F2A 108.3(5) . . ?
F4A C9A F3A 107.6(5) . . ?
F2A C9A F3A 106.6(5) . . ?
F4A C9A C7A 112.2(5) . . ?
F2A C9A C7A 109.6(5) . . ?
F3A C9A C7A 112.3(5) . . ?
N2B N1B C3B 113.4(5) . . ?
N2B N1B H1NB 114(4) . . ?
C3B N1B H1NB 133(4) . . ?
N1B N2B C1B 104.0(5) . . ?
C4B N3B C6B 118.5(5) . . ?
C4B N3B C5B 124.4(5) . . ?
C6B N3B C5B 117.0(5) . . ?
N2B C1B C2B 112.2(5) . . ?
N2B C1B C7B 121.5(5) . . ?
C2B C1B C7B 126.3(5) . . ?
C3B C2B C1B 103.7(5) . . ?
C3B C2B H2B 128.1 . . ?
C1B C2B H2B 128.1 . . ?
N1B C3B C2B 106.7(5) . . ?
N1B C3B C4B 115.9(5) . . ?
C2B C3B C4B 137.3(5) . . ?
O1B C4B N3B 122.1(5) . . ?
O1B C4B C3B 118.0(5) . . ?
N3B C4B C3B 119.9(5) . . ?
N3B C5B H5BA 109.5 . . ?
N3B C5B H5BB 109.5 . . ?
H5BA C5B H5BB 109.5 . . ?
N3B C5B H5BC 109.5 . . ?
H5BA C5B H5BC 109.5 . . ?
H5BB C5B H5BC 109.5 . . ?
N3B C6B H6BA 109.5 . . ?
N3B C6B H6BB 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
N3B C6B H6BC 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
F1B C7B C1B 108.6(4) . . ?
F1B C7B C9B 105.5(6) . . ?
C1B C7B C9B 112.5(5) . . ?
F1B C7B C8B 104.0(5) . . ?
C1B C7B C8B 112.6(5) . . ?
C9B C7B C8B 112.9(6) . . ?
F7B C8B F5B 108.9(6) . . ?
F7B C8B F6B 108.5(8) . . ?
F5B C8B F6B 108.2(6) . . ?
F7B C8B C7B 112.9(6) . . ?
F5B C8B C7B 110.7(6) . . ?
F6B C8B C7B 107.6(6) . . ?
F4B C9B F3B 109.7(7) . . ?
F4B C9B F2B 105.6(7) . . ?
F3B C9B F2B 107.1(6) . . ?
F4B C9B C7B 112.5(6) . . ?
F3B C9B C7B 113.9(6) . . ?
F2B C9B C7B 107.5(7) . . ?
N2C N1C C3C 114.7(5) . . ?
N2C N1C H1NC 128(4) . . ?
C3C N1C H1NC 117(4) . . ?
N1C N2C C1C 103.5(5) . . ?
C4C N3C C6C 119.3(5) . . ?
C4C N3C C5C 124.5(5) . . ?
C6C N3C C5C 116.1(5) . . ?
N2C C1C C2C 112.9(5) . . ?
N2C C1C C7C 116.6(6) . . ?
C2C C1C C7C 130.5(6) . . ?
C3C C2C C1C 103.6(6) . . ?
C3C C2C H2C 128.2 . . ?
C1C C2C H2C 128.2 . . ?
N1C C3C C2C 105.3(5) . . ?
N1C C3C C4C 116.1(5) . . ?
C2C C3C C4C 138.4(6) . . ?
O1C C4C N3C 121.9(5) . . ?
O1C C4C C3C 116.5(5) . . ?
N3C C4C C3C 121.5(5) . . ?
N3C C5C H5CA 109.5 . . ?
N3C C5C H5CB 109.5 . . ?
H5CA C5C H5CB 109.5 . . ?
N3C C5C H5CC 109.5 . . ?
H5CA C5C H5CC 109.5 . . ?
H5CB C5C H5CC 109.5 . . ?
N3C C6C H6CA 109.5 . . ?
N3C C6C H6CB 109.5 . . ?
H6CA C6C H6CB 109.5 . . ?
N3C C6C H6CC 109.5 . . ?
H6CA C6C H6CC 109.5 . . ?
H6CB C6C H6CC 109.5 . . ?
F1C C7C C8C 103.2(6) . . ?
F1C C7C C1C 110.7(6) . . ?
C8C C7C C1C 110.7(5) . . ?
F1C C7C C9C 105.0(5) . . ?
C8C C7C C9C 113.8(6) . . ?
C1C C7C C9C 112.8(5) . . ?
F2C C8C F3C 106.3(6) . . ?
F2C C8C F4C 112.6(7) . . ?
F3C C8C F4C 109.9(7) . . ?
F2C C8C C7C 110.3(7) . . ?
F3C C8C C7C 112.3(6) . . ?
F4C C8C C7C 105.6(6) . . ?
F7C C9C F6C 107.5(5) . . ?
F7C C9C F5C 107.6(5) . . ?
F6C C9C F5C 107.8(6) . . ?
F7C C9C C7C 108.6(6) . . ?
F6C C9C C7C 112.3(5) . . ?
F5C C9C C7C 112.8(5) . . ?
N2D N1D C3D 112.9(4) . . ?
N2D N1D H1ND 127(4) . . ?
C3D N1D H1ND 120(4) . . ?
C1D N2D N1D 104.6(4) . . ?
C4D N3D C6D 119.8(5) . . ?
C4D N3D C5D 124.6(4) . . ?
C6D N3D C5D 115.6(5) . . ?
N2D C1D C2D 112.4(5) . . ?
N2D C1D C7D 120.6(5) . . ?
C2D C1D C7D 127.0(5) . . ?
C3D C2D C1D 104.4(5) . . ?
C3D C2D H2D 127.8 . . ?
C1D C2D H2D 127.8 . . ?
N1D C3D C2D 105.6(4) . . ?
N1D C3D C4D 116.6(5) . . ?
C2D C3D C4D 137.6(5) . . ?
O1D C4D N3D 123.0(5) . . ?
O1D C4D C3D 117.4(5) . . ?
N3D C4D C3D 119.6(5) . . ?
N3D C5D H5DA 109.5 . . ?
N3D C5D H5DB 109.5 . . ?
H5DA C5D H5DB 109.5 . . ?
N3D C5D H5DC 109.5 . . ?
H5DA C5D H5DC 109.5 . . ?
H5DB C5D H5DC 109.5 . . ?
N3D C6D H6DA 109.5 . . ?
N3D C6D H6DB 109.5 . . ?
H6DA C6D H6DB 109.5 . . ?
N3D C6D H6DC 109.5 . . ?
H6DA C6D H6DC 109.5 . . ?
H6DB C6D H6DC 109.5 . . ?
F1D C7D C1D 108.7(4) . . ?
F1D C7D C9D 105.6(4) . . ?
C1D C7D C9D 111.2(4) . . ?
F1D C7D C8D 105.3(5) . . ?
C1D C7D C8D 113.1(4) . . ?
C9D C7D C8D 112.4(4) . . ?
F7D C8D F6D 108.5(5) . . ?
F7D C8D F5D 107.9(5) . . ?
F6D C8D F5D 108.0(5) . . ?
F7D C8D C7D 110.6(5) . . ?
F6D C8D C7D 111.6(5) . . ?
F5D C8D C7D 110.2(5) . . ?
F4D C9D F3D 108.2(5) . . ?
F4D C9D F2D 107.5(5) . . ?
F3D C9D F2D 107.8(4) . . ?
F4D C9D C7D 111.9(5) . . ?
F3D C9D C7D 112.2(5) . . ?
F2D C9D C7D 109.0(4) . . ?

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
C3A N1A N2A C1A 0.1(6) . . . . ?
N1A N2A C1A C2A 0.4(6) . . . . ?
N1A N2A C1A C7A -179.7(5) . . . . ?
N2A C1A C2A C3A -0.7(6) . . . . ?
C7A C1A C2A C3A 179.4(5) . . . . ?
N2A N1A C3A C2A -0.6(7) . . . . ?
N2A N1A C3A C4A 176.8(5) . . . . ?
C1A C2A C3A N1A 0.7(6) . . . . ?
C1A C2A C3A C4A -175.6(6) . . . . ?
C5A N3A C4A O1A 177.3(7) . . . . ?
C6A N3A C4A O1A -2.1(8) . . . . ?
C5A N3A C4A C3A -5.4(9) . . . . ?
C6A N3A C4A C3A 175.1(5) . . . . ?
N1A C3A C4A O1A -3.0(7) . . . . ?
C2A C3A C4A O1A 173.2(6) . . . . ?
N1A C3A C4A N3A 179.7(5) . . . . ?
C2A C3A C4A N3A -4.1(10) . . . . ?
N2A C1A C7A F1A 147.3(5) . . . . ?
C2A C1A C7A F1A -32.8(8) . . . . ?
N2A C1A C7A C9A -96.4(6) . . . . ?
C2A C1A C7A C9A 83.4(7) . . . . ?
N2A C1A C7A C8A 30.4(8) . . . . ?
C2A C1A C7A C8A -149.7(6) . . . . ?
F1A C7A C8A F6A 172.0(4) . . . . ?
C1A C7A C8A F6A -69.2(6) . . . . ?
C9A C7A C8A F6A 57.2(7) . . . . ?
F1A C7A C8A F5A 51.7(6) . . . . ?
C1A C7A C8A F5A 170.5(5) . . . . ?
C9A C7A C8A F5A -63.2(7) . . . . ?
F1A C7A C8A F7A -66.7(7) . . . . ?
C1A C7A C8A F7A 52.1(7) . . . . ?
C9A C7A C8A F7A 178.4(5) . . . . ?
F1A C7A C9A F4A 179.0(4) . . . . ?
C1A C7A C9A F4A 60.8(6) . . . . ?
C8A C7A C9A F4A -66.1(6) . . . . ?
F1A C7A C9A F2A 58.7(6) . . . . ?
C1A C7A C9A F2A -59.5(6) . . . . ?
C8A C7A C9A F2A 173.6(5) . . . . ?
F1A C7A C9A F3A -59.6(6) . . . . ?
C1A C7A C9A F3A -177.8(5) . . . . ?
C8A C7A C9A F3A 55.3(7) . . . . ?
C3B N1B N2B C1B 1.0(6) . . . . ?
N1B N2B C1B C2B -0.6(6) . . . . ?
N1B N2B C1B C7B -179.1(5) . . . . ?
N2B C1B C2B C3B 0.0(6) . . . . ?
C7B C1B C2B C3B 178.4(5) . . . . ?
N2B N1B C3B C2B -1.0(6) . . . . ?
N2B N1B C3B C4B -177.3(4) . . . . ?
C1B C2B C3B N1B 0.5(6) . . . . ?
C1B C2B C3B C4B 175.6(6) . . . . ?
C6B N3B C4B O1B 1.1(8) . . . . ?
C5B N3B C4B O1B 177.8(5) . . . . ?
C6B N3B C4B C3B -177.9(5) . . . . ?
C5B N3B C4B C3B -1.2(8) . . . . ?
N1B C3B C4B O1B 28.0(7) . . . . ?
C2B C3B C4B O1B -146.8(7) . . . . ?
N1B C3B C4B N3B -153.0(5) . . . . ?
C2B C3B C4B N3B 32.3(9) . . . . ?
N2B C1B C7B F1B -171.2(5) . . . . ?
C2B C1B C7B F1B 10.5(8) . . . . ?
N2B C1B C7B C9B 72.4(8) . . . . ?
C2B C1B C7B C9B -105.9(7) . . . . ?
N2B C1B C7B C8B -56.5(7) . . . . ?
C2B C1B C7B C8B 125.2(6) . . . . ?
F1B C7B C8B F7B 67.1(9) . . . . ?
C1B C7B C8B F7B -50.3(9) . . . . ?
C9B C7B C8B F7B -179.0(7) . . . . ?
F1B C7B C8B F5B -55.3(7) . . . . ?
C1B C7B C8B F5B -172.7(5) . . . . ?
C9B C7B C8B F5B 58.6(8) . . . . ?
F1B C7B C8B F6B -173.3(5) . . . . ?
C1B C7B C8B F6B 69.3(6) . . . . ?
C9B C7B C8B F6B -59.4(8) . . . . ?
F1B C7B C9B F4B -177.8(7) . . . . ?
C1B C7B C9B F4B -59.6(9) . . . . ?
C8B C7B C9B F4B 69.2(9) . . . . ?
F1B C7B C9B F3B 56.5(8) . . . . ?
C1B C7B C9B F3B 174.7(6) . . . . ?
C8B C7B C9B F3B -56.5(10) . . . . ?
F1B C7B C9B F2B -62.0(7) . . . . ?
C1B C7B C9B F2B 56.2(8) . . . . ?
C8B C7B C9B F2B -175.0(6) . . . . ?
C3C N1C N2C C1C -0.6(7) . . . . ?
N1C N2C C1C C2C -0.5(7) . . . . ?
N1C N2C C1C C7C 177.4(5) . . . . ?
N2C C1C C2C C3C 1.3(7) . . . . ?
C7C C1C C2C C3C -176.2(6) . . . . ?
N2C N1C C3C C2C 1.4(7) . . . . ?
N2C N1C C3C C4C 178.2(5) . . . . ?
C1C C2C C3C N1C -1.5(6) . . . . ?
C1C C2C C3C C4C -177.2(6) . . . . ?
C6C N3C C4C O1C -4.6(9) . . . . ?
C5C N3C C4C O1C 178.9(8) . . . . ?
C6C N3C C4C C3C 179.2(5) . . . . ?
C5C N3C C4C C3C 2.7(10) . . . . ?
N1C C3C C4C O1C -5.7(7) . . . . ?
C2C C3C C4C O1C 169.6(7) . . . . ?
N1C C3C C4C N3C 170.7(5) . . . . ?
C2C C3C C4C N3C -13.9(10) . . . . ?
N2C C1C C7C F1C 13.1(8) . . . . ?
C2C C1C C7C F1C -169.5(6) . . . . ?
N2C C1C C7C C8C -100.7(8) . . . . ?
C2C C1C C7C C8C 76.7(9) . . . . ?
N2C C1C C7C C9C 130.5(6) . . . . ?
C2C C1C C7C C9C -52.1(10) . . . . ?
F1C C7C C8C F2C -63.6(7) . . . . ?
C1C C7C C8C F2C 54.9(9) . . . . ?
C9C C7C C8C F2C -176.8(6) . . . . ?
F1C C7C C8C F3C 54.8(8) . . . . ?
C1C C7C C8C F3C 173.3(6) . . . . ?
C9C C7C C8C F3C -58.5(9) . . . . ?
F1C C7C C8C F4C 174.6(5) . . . . ?
C1C C7C C8C F4C -67.0(7) . . . . ?
C9C C7C C8C F4C 61.3(7) . . . . ?
F1C C7C C9C F7C 53.7(6) . . . . ?
C8C C7C C9C F7C 165.8(6) . . . . ?
C1C C7C C9C F7C -67.0(7) . . . . ?
F1C C7C C9C F6C 172.4(5) . . . . ?
C8C C7C C9C F6C -75.4(7) . . . . ?
C1C C7C C9C F6C 51.8(8) . . . . ?
F1C C7C C9C F5C -65.5(7) . . . . ?
C8C C7C C9C F5C 46.7(8) . . . . ?
C1C C7C C9C F5C 173.8(6) . . . . ?
C3D N1D N2D C1D -0.2(6) . . . . ?
N1D N2D C1D C2D -0.7(6) . . . . ?
N1D N2D C1D C7D -179.0(5) . . . . ?
N2D C1D C2D C3D 1.3(6) . . . . ?
C7D C1D C2D C3D 179.4(5) . . . . ?
N2D N1D C3D C2D 1.0(6) . . . . ?
N2D N1D C3D C4D 178.0(5) . . . . ?
C1D C2D C3D N1D -1.3(6) . . . . ?
C1D C2D C3D C4D -177.3(6) . . . . ?
C6D N3D C4D O1D -3.0(9) . . . . ?
C5D N3D C4D O1D -179.7(6) . . . . ?
C6D N3D C4D C3D 178.8(5) . . . . ?
C5D N3D C4D C3D 2.1(8) . . . . ?
N1D C3D C4D O1D -21.6(8) . . . . ?
C2D C3D C4D O1D 154.1(7) . . . . ?
N1D C3D C4D N3D 156.7(5) . . . . ?
C2D C3D C4D N3D -27.6(10) . . . . ?
N2D C1D C7D F1D -146.5(5) . . . . ?
C2D C1D C7D F1D 35.5(7) . . . . ?
N2D C1D C7D C9D 97.7(6) . . . . ?
C2D C1D C7D C9D -80.3(7) . . . . ?
N2D C1D C7D C8D -29.9(7) . . . . ?
C2D C1D C7D C8D 152.1(5) . . . . ?
F1D C7D C8D F7D 68.4(6) . . . . ?
C1D C7D C8D F7D -50.2(7) . . . . ?
C9D C7D C8D F7D -177.1(5) . . . . ?
F1D C7D C8D F6D -170.8(4) . . . . ?
C1D C7D C8D F6D 70.7(6) . . . . ?
C9D C7D C8D F6D -56.3(6) . . . . ?
F1D C7D C8D F5D -50.8(6) . . . . ?
C1D C7D C8D F5D -169.4(5) . . . . ?
C9D C7D C8D F5D 63.7(6) . . . . ?
F1D C7D C9D F4D -176.6(4) . . . . ?
C1D C7D C9D F4D -58.9(6) . . . . ?
C8D C7D C9D F4D 69.1(6) . . . . ?
F1D C7D C9D F3D 61.5(6) . . . . ?
C1D C7D C9D F3D 179.2(5) . . . . ?
C8D C7D C9D F3D -52.8(7) . . . . ?
F1D C7D C9D F2D -57.9(6) . . . . ?
C1D C7D C9D F2D 59.8(6) . . . . ?
C8D C7D C9D F2D -172.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1NA O1D 0.84(8) 1.92(8) 2.758(7) 171(7) .
N1B H1NB O1C 1.00(8) 1.79(8) 2.783(7) 170(6) .
N1C H1NC O1A 0.97(7) 1.93(7) 2.797(7) 148(6) .
N1D H1ND O1B 0.88(7) 1.95(7) 2.704(6) 144(6) .

_refine_diff_density_max         0.633
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.072
####################################################################### 
# 
# 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_tolm324
_database_code_depnum_ccdc_archive 'CCDC 1541690'
_audit_update_record             
;
2017-06-23 deposited with the CCDC.
2017-07-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 F7 N2 O'
_chemical_formula_weight         354.23

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'
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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   9.3738(14)
_cell_length_b                   12.4038(13)
_cell_length_c                   14.0939(14)
_cell_angle_alpha                104.197(9)
_cell_angle_beta                 90.841(11)
_cell_angle_gamma                101.985(11)
_cell_volume                     1550.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             712
_exptl_absorpt_coefficient_mu    0.155
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9698
_exptl_absorpt_correction_T_max  0.9908
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15893
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_sigmaI/netI    0.0998
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         30.00
_reflns_number_total             8922
_reflns_number_gt                2608
_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)+(0.0981P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0060(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         8922
_refine_ls_number_parameters     444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2191
_refine_ls_R_factor_gt           0.0701
_refine_ls_wR_factor_ref         0.2410
_refine_ls_wR_factor_gt          0.1765
_refine_ls_goodness_of_fit_ref   0.819
_refine_ls_restrained_S_all      0.819
_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
F1A F 0.2812(4) 1.2197(2) 0.23410(17) 0.1578(12) Uani 1 1 d . . .
F2A F 0.0585(6) 1.0380(8) 0.1344(5) 0.310(4) Uani 1 1 d . . .
F3A F 0.2153(8) 0.9769(4) 0.0424(3) 0.272(4) Uani 1 1 d . . .
F4A F 0.1717(6) 1.1444(3) 0.0522(2) 0.251(2) Uani 1 1 d . . .
F5A F 0.4965(6) 1.0572(5) 0.1067(4) 0.247(3) Uani 1 1 d . . .
F6A F 0.4584(5) 1.2116(3) 0.0897(3) 0.241(2) Uani 1 1 d . . .
F7A F 0.5442(6) 1.1919(5) 0.2250(5) 0.262(3) Uani 1 1 d . . .
O1A O 0.3629(2) 0.87174(16) 0.48742(15) 0.0833(6) Uani 1 1 d . . .
N1A N 0.2936(3) 0.8939(2) 0.30274(19) 0.0780(8) Uani 1 1 d . . .
H1NA H 0.307(3) 0.834(2) 0.3008(19) 0.061(8) Uiso 1 1 d . . .
N2A N 0.2925(3) 0.9297(2) 0.22101(19) 0.0920(9) Uani 1 1 d . . .
C1A C 0.2943(4) 1.0403(2) 0.2537(2) 0.0782(9) Uani 1 1 d . . .
C2A C 0.2966(3) 1.0745(2) 0.3551(2) 0.0727(8) Uani 1 1 d . . .
H2A H 0.2977 1.1471 0.3939 0.087 Uiso 1 1 calc R . .
C3A C 0.2968(3) 0.9770(2) 0.3858(2) 0.0684(7) Uani 1 1 d . . .
C4A C 0.3122(3) 0.9538(2) 0.4818(2) 0.0648(7) Uani 1 1 d . . .
C5A C 0.2718(3) 1.0301(2) 0.5704(2) 0.0668(7) Uani 1 1 d . . .
C6A C 0.1730(3) 1.0988(3) 0.5669(2) 0.0779(8) Uani 1 1 d . . .
H6A H 0.1316 1.0991 0.5066 0.093 Uiso 1 1 calc R . .
C7A C 0.1358(4) 1.1668(3) 0.6523(3) 0.0895(10) Uani 1 1 d . . .
H7A H 0.0689 1.2117 0.6486 0.107 Uiso 1 1 calc R . .
C8A C 0.1963(4) 1.1691(3) 0.7426(3) 0.0875(9) Uani 1 1 d . . .
C9A C 0.2938(4) 1.0993(3) 0.7466(2) 0.0894(10) Uani 1 1 d . . .
H9A H 0.3358 1.0994 0.8068 0.107 Uiso 1 1 calc R . .
C10A C 0.3283(3) 1.0302(3) 0.6617(2) 0.0778(8) Uani 1 1 d . . .
H10A H 0.3912 0.9823 0.6658 0.093 Uiso 1 1 calc R . .
C11A C 0.1578(6) 1.2445(4) 0.8343(3) 0.1256(14) Uani 1 1 d . . .
H11C H 0.0618 1.2575 0.8245 0.188 Uiso 1 1 calc R . .
H11B H 0.2275 1.3160 0.8502 0.188 Uiso 1 1 calc R . .
H11A H 0.1593 1.2085 0.8872 0.188 Uiso 1 1 calc R . .
C12A C 0.2991(6) 1.1134(3) 0.1828(3) 0.1031(12) Uani 1 1 d . . .
C13A C 0.1748(13) 1.0741(7) 0.1074(6) 0.207(4) Uani 1 1 d . . .
C14A C 0.4543(11) 1.1409(6) 0.1497(6) 0.170(3) Uani 1 1 d . . .
F1B F 0.3520(3) 0.43560(19) 0.07436(16) 0.1355(9) Uani 1 1 d . . .
F2B F 0.4478(4) 0.6622(3) 0.0654(2) 0.1732(13) Uani 1 1 d . . .
F3B F 0.2373(4) 0.6903(2) 0.09864(18) 0.1467(10) Uani 1 1 d . . .
F4B F 0.2634(3) 0.5630(2) -0.02765(17) 0.1489(10) Uani 1 1 d . . .
F5B F 0.0727(3) 0.5473(3) 0.1876(2) 0.1580(11) Uani 1 1 d . . .
F6B F 0.0660(3) 0.4244(2) 0.0520(2) 0.1643(11) Uani 1 1 d . . .
F7B F 0.1376(3) 0.3929(2) 0.1872(3) 0.1676(12) Uani 1 1 d . . .
O1B O 0.6328(3) 0.66194(19) 0.51305(18) 0.0960(7) Uani 1 1 d . . .
N1B N 0.4654(3) 0.6816(2) 0.3624(2) 0.0734(7) Uani 1 1 d . . .
H1NB H 0.476(3) 0.734(2) 0.410(2) 0.056(8) Uiso 1 1 d . . .
N2B N 0.3734(3) 0.6712(2) 0.2864(2) 0.0774(7) Uani 1 1 d . . .
C1B C 0.3842(3) 0.5733(2) 0.2251(2) 0.0744(8) Uani 1 1 d . . .
C2B C 0.4827(3) 0.5220(3) 0.2639(2) 0.0787(9) Uani 1 1 d . . .
H2B H 0.5074 0.4529 0.2354 0.094 Uiso 1 1 calc R . .
C3B C 0.5346(3) 0.5944(2) 0.3520(2) 0.0706(8) Uani 1 1 d . . .
C4B C 0.6324(3) 0.5926(2) 0.4356(2) 0.0724(8) Uani 1 1 d . . .
C5B C 0.7218(3) 0.5058(2) 0.4244(3) 0.0747(8) Uani 1 1 d . . .
C6B C 0.7673(4) 0.4529(3) 0.3358(3) 0.0943(10) Uani 1 1 d . . .
H6B H 0.7438 0.4728 0.2790 0.113 Uiso 1 1 calc R . .
C7B C 0.8477(4) 0.3705(3) 0.3312(3) 0.1064(12) Uani 1 1 d . . .
H7B H 0.8768 0.3355 0.2707 0.128 Uiso 1 1 calc R . .
C8B C 0.8860(4) 0.3385(3) 0.4124(4) 0.0953(11) Uani 1 1 d . . .
C9B C 0.8434(4) 0.3928(3) 0.4999(3) 0.0959(11) Uani 1 1 d . . .
H9B H 0.8689 0.3733 0.5565 0.115 Uiso 1 1 calc R . .
C10B C 0.7632(3) 0.4761(3) 0.5072(3) 0.0860(9) Uani 1 1 d . . .
H10B H 0.7371 0.5123 0.5683 0.103 Uiso 1 1 calc R . .
C11B C 0.9730(4) 0.2482(3) 0.4073(4) 0.1331(17) Uani 1 1 d . . .
H11E H 1.0032 0.2253 0.3420 0.200 Uiso 1 1 calc R . .
H11D H 0.9135 0.1835 0.4242 0.200 Uiso 1 1 calc R . .
H11F H 1.0576 0.2781 0.4526 0.200 Uiso 1 1 calc R . .
C12B C 0.2963(4) 0.5265(3) 0.1281(3) 0.0882(10) Uani 1 1 d . . .
C13B C 0.3127(6) 0.6110(4) 0.0638(3) 0.1106(12) Uani 1 1 d . . .
C14B C 0.1405(5) 0.4723(4) 0.1393(4) 0.1211(15) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1A C12A 1.384(4) . ?
F2A C13A 1.196(11) . ?
F3A C13A 1.447(12) . ?
F4A C13A 1.308(6) . ?
F5A C14A 1.213(7) . ?
F6A C14A 1.356(6) . ?
F7A C14A 1.288(8) . ?
O1A C4A 1.228(3) . ?
N1A N2A 1.333(3) . ?
N1A C3A 1.353(4) . ?
N2A C1A 1.333(4) . ?
C1A C2A 1.386(4) . ?
C1A C12A 1.500(4) . ?
C2A C3A 1.381(3) . ?
C3A C4A 1.462(4) . ?
C4A C5A 1.477(4) . ?
C5A C10A 1.384(4) . ?
C5A C6A 1.390(4) . ?
C6A C7A 1.385(4) . ?
C7A C8A 1.376(5) . ?
C8A C9A 1.393(4) . ?
C8A C11A 1.496(4) . ?
C9A C10A 1.376(4) . ?
C12A C13A 1.482(8) . ?
C12A C14A 1.530(9) . ?
F1B C12B 1.398(3) . ?
F2B C13B 1.290(5) . ?
F3B C13B 1.330(5) . ?
F4B C13B 1.312(4) . ?
F5B C14B 1.296(5) . ?
F6B C14B 1.340(5) . ?
F7B C14B 1.321(5) . ?
O1B C4B 1.212(3) . ?
N1B N2B 1.329(3) . ?
N1B C3B 1.352(3) . ?
N2B C1B 1.330(3) . ?
C1B C2B 1.400(4) . ?
C1B C12B 1.505(5) . ?
C2B C3B 1.356(4) . ?
C3B C4B 1.490(4) . ?
C4B C5B 1.476(4) . ?
C5B C6B 1.379(4) . ?
C5B C10B 1.381(4) . ?
C6B C7B 1.381(4) . ?
C7B C8B 1.366(5) . ?
C8B C9B 1.361(5) . ?
C8B C11B 1.505(5) . ?
C9B C10B 1.385(4) . ?
C12B C14B 1.504(6) . ?
C12B C13B 1.531(5) . ?

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
N2A N1A C3A 113.8(2) . . ?
N1A N2A C1A 103.6(3) . . ?
N2A C1A C2A 112.4(3) . . ?
N2A C1A C12A 120.1(3) . . ?
C2A C1A C12A 127.5(3) . . ?
C3A C2A C1A 104.8(2) . . ?
N1A C3A C2A 105.4(3) . . ?
N1A C3A C4A 120.3(2) . . ?
C2A C3A C4A 134.0(3) . . ?
O1A C4A C3A 118.7(3) . . ?
O1A C4A C5A 121.0(2) . . ?
C3A C4A C5A 120.3(2) . . ?
C10A C5A C6A 117.9(3) . . ?
C10A C5A C4A 119.3(3) . . ?
C6A C5A C4A 122.8(3) . . ?
C7A C6A C5A 120.6(3) . . ?
C8A C7A C6A 121.1(3) . . ?
C7A C8A C9A 118.5(3) . . ?
C7A C8A C11A 120.8(3) . . ?
C9A C8A C11A 120.7(3) . . ?
C10A C9A C8A 120.2(3) . . ?
C9A C10A C5A 121.7(3) . . ?
F1A C12A C13A 103.4(6) . . ?
F1A C12A C1A 108.1(3) . . ?
C13A C12A C1A 113.6(4) . . ?
F1A C12A C14A 102.1(4) . . ?
C13A C12A C14A 118.6(6) . . ?
C1A C12A C14A 109.6(4) . . ?
F2A C13A F4A 114.2(11) . . ?
F2A C13A F3A 105.6(8) . . ?
F4A C13A F3A 104.0(8) . . ?
F2A C13A C12A 116.2(7) . . ?
F4A C13A C12A 113.2(6) . . ?
F3A C13A C12A 101.7(9) . . ?
F5A C14A F7A 107.6(9) . . ?
F5A C14A F6A 108.6(6) . . ?
F7A C14A F6A 108.5(6) . . ?
F5A C14A C12A 113.5(6) . . ?
F7A C14A C12A 109.7(6) . . ?
F6A C14A C12A 108.8(7) . . ?
N2B N1B C3B 113.6(3) . . ?
N1B N2B C1B 103.9(2) . . ?
N2B C1B C2B 111.4(3) . . ?
N2B C1B C12B 122.3(3) . . ?
C2B C1B C12B 126.3(3) . . ?
C3B C2B C1B 105.3(3) . . ?
N1B C3B C2B 105.8(3) . . ?
N1B C3B C4B 118.4(3) . . ?
C2B C3B C4B 135.5(3) . . ?
O1B C4B C5B 121.5(3) . . ?
O1B C4B C3B 118.1(3) . . ?
C5B C4B C3B 120.4(3) . . ?
C6B C5B C10B 117.8(3) . . ?
C6B C5B C4B 123.8(3) . . ?
C10B C5B C4B 118.4(3) . . ?
C5B C6B C7B 120.2(4) . . ?
C8B C7B C6B 122.3(4) . . ?
C9B C8B C7B 117.2(3) . . ?
C9B C8B C11B 120.5(4) . . ?
C7B C8B C11B 122.3(4) . . ?
C8B C9B C10B 122.0(3) . . ?
C5B C10B C9B 120.4(4) . . ?
F1B C12B C14B 103.5(3) . . ?
F1B C12B C1B 107.9(3) . . ?
C14B C12B C1B 112.2(3) . . ?
F1B C12B C13B 104.6(3) . . ?
C14B C12B C13B 114.2(3) . . ?
C1B C12B C13B 113.4(3) . . ?
F2B C13B F4B 108.9(4) . . ?
F2B C13B F3B 107.5(4) . . ?
F4B C13B F3B 107.0(4) . . ?
F2B C13B C12B 110.6(4) . . ?
F4B C13B C12B 113.1(4) . . ?
F3B C13B C12B 109.5(4) . . ?
F5B C14B F7B 108.7(5) . . ?
F5B C14B F6B 107.2(4) . . ?
F7B C14B F6B 108.7(4) . . ?
F5B C14B C12B 110.9(4) . . ?
F7B C14B C12B 109.7(3) . . ?
F6B C14B C12B 111.6(4) . . ?

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
C3A N1A N2A C1A -0.3(4) . . . . ?
N1A N2A C1A C2A 0.1(4) . . . . ?
N1A N2A C1A C12A 177.8(3) . . . . ?
N2A C1A C2A C3A 0.2(4) . . . . ?
C12A C1A C2A C3A -177.4(4) . . . . ?
N2A N1A C3A C2A 0.5(4) . . . . ?
N2A N1A C3A C4A -174.2(3) . . . . ?
C1A C2A C3A N1A -0.4(3) . . . . ?
C1A C2A C3A C4A 173.2(3) . . . . ?
N1A C3A C4A O1A 20.5(4) . . . . ?
C2A C3A C4A O1A -152.4(3) . . . . ?
N1A C3A C4A C5A -161.5(3) . . . . ?
C2A C3A C4A C5A 25.7(5) . . . . ?
O1A C4A C5A C10A 18.5(4) . . . . ?
C3A C4A C5A C10A -159.5(3) . . . . ?
O1A C4A C5A C6A -158.3(3) . . . . ?
C3A C4A C5A C6A 23.7(4) . . . . ?
C10A C5A C6A C7A 1.5(5) . . . . ?
C4A C5A C6A C7A 178.3(3) . . . . ?
C5A C6A C7A C8A 0.6(5) . . . . ?
C6A C7A C8A C9A -1.4(5) . . . . ?
C6A C7A C8A C11A 178.8(3) . . . . ?
C7A C8A C9A C10A 0.1(5) . . . . ?
C11A C8A C9A C10A 179.9(3) . . . . ?
C8A C9A C10A C5A 2.0(5) . . . . ?
C6A C5A C10A C9A -2.8(5) . . . . ?
C4A C5A C10A C9A -179.8(3) . . . . ?
N2A C1A C12A F1A 172.5(3) . . . . ?
C2A C1A C12A F1A -10.1(6) . . . . ?
N2A C1A C12A C13A 58.4(8) . . . . ?
C2A C1A C12A C13A -124.2(7) . . . . ?
N2A C1A C12A C14A -77.0(5) . . . . ?
C2A C1A C12A C14A 100.5(5) . . . . ?
F1A C12A C13A F2A -78.5(11) . . . . ?
C1A C12A C13A F2A 38.4(14) . . . . ?
C14A C12A C13A F2A 169.4(10) . . . . ?
F1A C12A C13A F4A 56.6(11) . . . . ?
C1A C12A C13A F4A 173.5(8) . . . . ?
C14A C12A C13A F4A -55.5(12) . . . . ?
F1A C12A C13A F3A 167.5(5) . . . . ?
C1A C12A C13A F3A -75.6(7) . . . . ?
C14A C12A C13A F3A 55.4(6) . . . . ?
F1A C12A C14A F5A 176.4(6) . . . . ?
C13A C12A C14A F5A -70.8(8) . . . . ?
C1A C12A C14A F5A 62.0(8) . . . . ?
F1A C12A C14A F7A 56.0(6) . . . . ?
C13A C12A C14A F7A 168.8(6) . . . . ?
C1A C12A C14A F7A -58.4(6) . . . . ?
F1A C12A C14A F6A -62.5(6) . . . . ?
C13A C12A C14A F6A 50.3(8) . . . . ?
C1A C12A C14A F6A -176.9(4) . . . . ?
C3B N1B N2B C1B 0.1(3) . . . . ?
N1B N2B C1B C2B 0.6(3) . . . . ?
N1B N2B C1B C12B 179.4(3) . . . . ?
N2B C1B C2B C3B -1.1(4) . . . . ?
C12B C1B C2B C3B -179.8(3) . . . . ?
N2B N1B C3B C2B -0.8(4) . . . . ?
N2B N1B C3B C4B -175.7(2) . . . . ?
C1B C2B C3B N1B 1.1(3) . . . . ?
C1B C2B C3B C4B 174.7(3) . . . . ?
N1B C3B C4B O1B 8.3(4) . . . . ?
C2B C3B C4B O1B -164.7(4) . . . . ?
N1B C3B C4B C5B -173.8(3) . . . . ?
C2B C3B C4B C5B 13.2(5) . . . . ?
O1B C4B C5B C6B -156.2(3) . . . . ?
C3B C4B C5B C6B 26.0(5) . . . . ?
O1B C4B C5B C10B 23.4(5) . . . . ?
C3B C4B C5B C10B -154.4(3) . . . . ?
C10B C5B C6B C7B 2.0(5) . . . . ?
C4B C5B C6B C7B -178.4(3) . . . . ?
C5B C6B C7B C8B -0.4(6) . . . . ?
C6B C7B C8B C9B -0.9(6) . . . . ?
C6B C7B C8B C11B 179.7(3) . . . . ?
C7B C8B C9B C10B 0.7(5) . . . . ?
C11B C8B C9B C10B -179.9(3) . . . . ?
C6B C5B C10B C9B -2.3(5) . . . . ?
C4B C5B C10B C9B 178.1(3) . . . . ?
C8B C9B C10B C5B 0.9(5) . . . . ?
N2B C1B C12B F1B 169.2(3) . . . . ?
C2B C1B C12B F1B -12.3(5) . . . . ?
N2B C1B C12B C14B -77.5(4) . . . . ?
C2B C1B C12B C14B 101.1(4) . . . . ?
N2B C1B C12B C13B 53.8(5) . . . . ?
C2B C1B C12B C13B -127.6(4) . . . . ?
F1B C12B C13B F2B -73.9(4) . . . . ?
C14B C12B C13B F2B 173.7(4) . . . . ?
C1B C12B C13B F2B 43.4(5) . . . . ?
F1B C12B C13B F4B 48.5(5) . . . . ?
C14B C12B C13B F4B -63.9(5) . . . . ?
C1B C12B C13B F4B 165.8(4) . . . . ?
F1B C12B C13B F3B 167.8(3) . . . . ?
C14B C12B C13B F3B 55.4(5) . . . . ?
C1B C12B C13B F3B -74.9(5) . . . . ?
F1B C12B C14B F5B -179.4(4) . . . . ?
C1B C12B C14B F5B 64.6(4) . . . . ?
C13B C12B C14B F5B -66.3(5) . . . . ?
F1B C12B C14B F7B 60.6(5) . . . . ?
C1B C12B C14B F7B -55.5(5) . . . . ?
C13B C12B C14B F7B 173.7(4) . . . . ?
F1B C12B C14B F6B -59.9(4) . . . . ?
C1B C12B C14B F6B -175.9(3) . . . . ?
C13B C12B C14B F6B 53.2(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.041
####################################################################### 
# 
# 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_t327
_database_code_depnum_ccdc_archive 'CCDC 1541686'
_audit_update_record             
;
2017-06-23 deposited with the CCDC.
2017-07-14 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 H11 F7 N2 O'
_chemical_formula_weight         320.22

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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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                   11.7601(6)
_cell_length_b                   10.6895(4)
_cell_length_c                   11.2243(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 110.252(6)
_cell_angle_gamma                90.00
_cell_volume                     1323.77(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.607
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9666
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            12935
_diffrn_reflns_av_R_equivalents  0.0531
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         30.00
_reflns_number_total             3780
_reflns_number_gt                2365
_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)+(0.0645P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3780
_refine_ls_number_parameters     197
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0480
_refine_ls_wR_factor_ref         0.1346
_refine_ls_wR_factor_gt          0.1151
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_restrained_S_all      0.942
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.43684(9) 0.79868(9) 0.44637(9) 0.0373(3) Uani 1 1 d . . .
F2 F 0.22893(11) 0.93673(10) 0.37105(13) 0.0520(3) Uani 1 1 d . . .
F3 F 0.38972(10) 1.04028(9) 0.38706(11) 0.0471(3) Uani 1 1 d . . .
F4 F 0.26104(10) 0.99710(10) 0.20352(11) 0.0462(3) Uani 1 1 d . . .
F5 F 0.56777(10) 0.92004(11) 0.33211(12) 0.0493(3) Uani 1 1 d . . .
F6 F 0.44079(10) 0.88354(12) 0.14590(11) 0.0489(3) Uani 1 1 d . . .
F7 F 0.53347(11) 0.73166(11) 0.26598(14) 0.0584(4) Uani 1 1 d . . .
O1 O 0.05419(12) 0.39966(11) 0.10769(13) 0.0414(3) Uani 1 1 d . . .
N1 N 0.16511(14) 0.62013(13) 0.11549(15) 0.0320(3) Uani 1 1 d . . .
H1N H 0.109(2) 0.6097(18) 0.044(2) 0.039(5) Uiso 1 1 d . . .
N2 N 0.22805(13) 0.72735(13) 0.13417(14) 0.0342(3) Uani 1 1 d . . .
C1 C 0.29329(14) 0.72508(15) 0.25838(16) 0.0287(3) Uani 1 1 d . . .
C2 C 0.27143(15) 0.61922(15) 0.31891(17) 0.0296(3) Uani 1 1 d . . .
H2 H 0.3062 0.5980 0.4063 0.035 Uiso 1 1 calc R . .
C3 C 0.18715(15) 0.55120(15) 0.22279(16) 0.0289(3) Uani 1 1 d . . .
C4 C 0.12130(15) 0.43182(15) 0.21352(17) 0.0301(4) Uani 1 1 d . . .
C5 C 0.13434(15) 0.35324(14) 0.33067(17) 0.0309(4) Uani 1 1 d . . .
C6 C 0.26752(16) 0.32237(17) 0.4043(2) 0.0398(4) Uani 1 1 d . . .
H6A H 0.3033 0.2816 0.3474 0.060 Uiso 1 1 calc R . .
H6B H 0.2726 0.2660 0.4748 0.060 Uiso 1 1 calc R . .
H6C H 0.3118 0.3997 0.4377 0.060 Uiso 1 1 calc R . .
C7 C 0.08014(18) 0.42748(17) 0.41584(19) 0.0386(4) Uani 1 1 d . . .
H7A H 0.0842 0.3768 0.4899 0.058 Uiso 1 1 calc R . .
H7B H -0.0046 0.4480 0.3677 0.058 Uiso 1 1 calc R . .
H7C H 0.1264 0.5048 0.4441 0.058 Uiso 1 1 calc R . .
C8 C 0.06433(17) 0.23111(16) 0.28908(19) 0.0387(4) Uani 1 1 d . . .
H8A H 0.0987 0.1841 0.2347 0.058 Uiso 1 1 calc R . .
H8B H -0.0210 0.2499 0.2418 0.058 Uiso 1 1 calc R . .
H8C H 0.0704 0.1810 0.3641 0.058 Uiso 1 1 calc R . .
C9 C 0.37977(15) 0.82939(15) 0.32000(16) 0.0301(4) Uani 1 1 d . . .
C10 C 0.31450(16) 0.95296(16) 0.32042(17) 0.0340(4) Uani 1 1 d . . .
C11 C 0.48145(16) 0.84236(17) 0.26444(18) 0.0374(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C9 1.3825(19) . ?
F2 C10 1.327(2) . ?
F3 C10 1.325(2) . ?
F4 C10 1.330(2) . ?
F5 C11 1.328(2) . ?
F6 C11 1.324(2) . ?
F7 C11 1.329(2) . ?
O1 C4 1.226(2) . ?
N1 N2 1.341(2) . ?
N1 C3 1.358(2) . ?
N2 C1 1.339(2) . ?
C1 C2 1.389(2) . ?
C1 C9 1.506(2) . ?
C2 C3 1.391(2) . ?
C3 C4 1.478(2) . ?
C4 C5 1.523(2) . ?
C5 C8 1.528(2) . ?
C5 C6 1.533(2) . ?
C5 C7 1.540(2) . ?
C9 C10 1.529(2) . ?
C9 C11 1.534(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
N2 N1 C3 113.55(15) . . ?
C1 N2 N1 103.51(14) . . ?
N2 C1 C2 112.82(14) . . ?
N2 C1 C9 121.14(14) . . ?
C2 C1 C9 126.04(15) . . ?
C1 C2 C3 104.44(15) . . ?
N1 C3 C2 105.68(14) . . ?
N1 C3 C4 118.14(15) . . ?
C2 C3 C4 136.18(16) . . ?
O1 C4 C3 117.16(16) . . ?
O1 C4 C5 121.37(15) . . ?
C3 C4 C5 121.46(14) . . ?
C4 C5 C8 108.97(15) . . ?
C4 C5 C6 111.29(14) . . ?
C8 C5 C6 108.83(14) . . ?
C4 C5 C7 108.19(13) . . ?
C8 C5 C7 109.57(14) . . ?
C6 C5 C7 109.97(15) . . ?
F1 C9 C1 107.83(13) . . ?
F1 C9 C10 105.55(13) . . ?
C1 C9 C10 112.41(14) . . ?
F1 C9 C11 105.58(14) . . ?
C1 C9 C11 112.18(14) . . ?
C10 C9 C11 112.71(13) . . ?
F3 C10 F2 107.91(15) . . ?
F3 C10 F4 107.59(14) . . ?
F2 C10 F4 107.41(15) . . ?
F3 C10 C9 111.88(15) . . ?
F2 C10 C9 110.15(14) . . ?
F4 C10 C9 111.71(14) . . ?
F6 C11 F5 107.80(15) . . ?
F6 C11 F7 108.27(15) . . ?
F5 C11 F7 106.97(15) . . ?
F6 C11 C9 112.17(15) . . ?
F5 C11 C9 111.90(15) . . ?
F7 C11 C9 109.52(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
C3 N1 N2 C1 0.58(18) . . . . ?
N1 N2 C1 C2 -0.87(18) . . . . ?
N1 N2 C1 C9 179.09(14) . . . . ?
N2 C1 C2 C3 0.83(19) . . . . ?
C9 C1 C2 C3 -179.12(15) . . . . ?
N2 N1 C3 C2 -0.09(19) . . . . ?
N2 N1 C3 C4 179.20(14) . . . . ?
C1 C2 C3 N1 -0.43(18) . . . . ?
C1 C2 C3 C4 -179.51(18) . . . . ?
N1 C3 C4 O1 3.0(2) . . . . ?
C2 C3 C4 O1 -177.98(19) . . . . ?
N1 C3 C4 C5 -175.86(15) . . . . ?
C2 C3 C4 C5 3.1(3) . . . . ?
O1 C4 C5 C8 6.0(2) . . . . ?
C3 C4 C5 C8 -175.15(15) . . . . ?
O1 C4 C5 C6 126.04(18) . . . . ?
C3 C4 C5 C6 -55.1(2) . . . . ?
O1 C4 C5 C7 -113.03(18) . . . . ?
C3 C4 C5 C7 65.80(19) . . . . ?
N2 C1 C9 F1 -177.69(14) . . . . ?
C2 C1 C9 F1 2.3(2) . . . . ?
N2 C1 C9 C10 66.4(2) . . . . ?
C2 C1 C9 C10 -113.66(18) . . . . ?
N2 C1 C9 C11 -61.9(2) . . . . ?
C2 C1 C9 C11 118.09(18) . . . . ?
F1 C9 C10 F3 55.69(17) . . . . ?
C1 C9 C10 F3 172.97(14) . . . . ?
C11 C9 C10 F3 -59.1(2) . . . . ?
F1 C9 C10 F2 -64.33(17) . . . . ?
C1 C9 C10 F2 52.95(19) . . . . ?
C11 C9 C10 F2 -179.08(14) . . . . ?
F1 C9 C10 F4 176.38(13) . . . . ?
C1 C9 C10 F4 -66.33(18) . . . . ?
C11 C9 C10 F4 61.64(19) . . . . ?
F1 C9 C11 F6 -173.96(13) . . . . ?
C1 C9 C11 F6 68.85(18) . . . . ?
C10 C9 C11 F6 -59.2(2) . . . . ?
F1 C9 C11 F5 -52.66(18) . . . . ?
C1 C9 C11 F5 -169.85(14) . . . . ?
C10 C9 C11 F5 62.1(2) . . . . ?
F1 C9 C11 F7 65.79(17) . . . . ?
C1 C9 C11 F7 -51.4(2) . . . . ?
C10 C9 C11 F7 -179.48(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.85(2) 2.08(2) 2.915(2) 166.0(19) 3_565

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.054
