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

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

data_exp_1997
_database_code_depnum_ccdc_archive 'CCDC 1454754'
_audit_update_record             
;
2016-02-19 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;
_audit_creation_date             2014-03-19
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C10 F8, C13 H11 N3 O'
_chemical_formula_sum            'C23 H11 F8 N3 O'
_chemical_formula_weight         497.35
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   6.5595(9)
_cell_length_b                   41.849(3)
_cell_length_c                   6.9922(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.939(8)
_cell_angle_gamma                90.00
_cell_volume                     1912.3(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1218
_cell_measurement_temperature    97.3
_cell_measurement_theta_max      29.4775
_cell_measurement_theta_min      2.9182
_exptl_absorpt_coefficient_mu    0.162
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1000
_exptl_crystal_size_max          0.70
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.01
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -50
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8680
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         2.96
_diffrn_ambient_temperature      97.3
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   38.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6043  -77.0000  -60.0000 174

#__ type_ start__ end____ width___ exp.time_
  2 omega   11.00   37.00   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6043  -37.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
  3 omega   -8.00   54.50   0.5000   13.0000
omega____ theta____ kappa____ phi______ frames
    -       18.6043   77.0000   60.0000 125
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0752113000
_diffrn_orient_matrix_UB_12      -0.0056861000
_diffrn_orient_matrix_UB_13      -0.0708228000
_diffrn_orient_matrix_UB_21      -0.0776224000
_diffrn_orient_matrix_UB_22      0.0074513000
_diffrn_orient_matrix_UB_23      0.0489735000
_diffrn_orient_matrix_UB_31      0.0107418000
_diffrn_orient_matrix_UB_32      0.0141286000
_diffrn_orient_matrix_UB_33      -0.0541217000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2728
_reflns_number_total             3752
_reflns_odcompleteness_completeness 90.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     318
_refine_ls_number_reflns         3752
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0642
_refine_ls_restrained_S_all      1.090
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0431P)²+1.4996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1452
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.1718(3) 0.09263(4) 0.4995(3) 0.0215(5) Uani 1 1 d . . .
F4 F -0.5950(3) 0.06048(4) 0.1943(3) 0.0225(5) Uani 1 1 d . . .
F5 F -0.6931(3) 0.12075(4) 0.1690(3) 0.0222(5) Uani 1 1 d . . .
F8 F 0.0710(3) 0.15222(4) 0.4853(3) 0.0242(5) Uani 1 1 d . . .
F2 F 0.0725(3) 0.03150(4) 0.4219(3) 0.0237(5) Uani 1 1 d . . .
F7 F -0.2128(3) 0.19723(4) 0.4023(3) 0.0242(5) Uani 1 1 d . . .
F3 F -0.3097(3) 0.01560(4) 0.2778(3) 0.0263(5) Uani 1 1 d . . .
F6 F -0.5921(3) 0.18187(4) 0.2463(3) 0.0241(5) Uani 1 1 d . . .
C23 C -0.3616(5) 0.10248(7) 0.2946(4) 0.0157(7) Uani 1 1 d . . .
C22 C -0.1613(5) 0.11069(7) 0.3757(4) 0.0149(7) Uani 1 1 d . . .
C19 C -0.4544(5) 0.15855(7) 0.2875(5) 0.0174(7) Uani 1 1 d . . .
C21 C -0.1166(5) 0.14340(7) 0.4103(4) 0.0164(7) Uani 1 1 d . . .
C15 C -0.0654(5) 0.05468(7) 0.3830(5) 0.0170(7) Uani 1 1 d . . .
C14 C -0.0171(5) 0.08588(7) 0.4185(4) 0.0159(7) Uani 1 1 d . . .
N1 N -0.1126(4) 0.12482(6) 0.8868(4) 0.0190(6) Uani 1 1 d . . .
C20 C -0.2591(5) 0.16646(7) 0.3690(5) 0.0188(7) Uani 1 1 d . . .
N2 N -0.3015(4) 0.13614(6) 0.8370(4) 0.0166(6) Uani 1 1 d . . .
O1 O -0.0104(3) 0.18258(5) 1.0124(4) 0.0246(6) Uani 1 1 d . . .
H1 H 0.0151 0.1635 0.9848 0.037 Uiso 1 1 calc R . .
C17 C -0.4065(5) 0.06971(8) 0.2641(5) 0.0173(7) Uani 1 1 d . . .
N3 N -0.4481(4) 0.11487(6) 0.7855(4) 0.0192(6) Uani 1 1 d . . .
C18 C -0.5033(5) 0.12724(7) 0.2511(4) 0.0159(7) Uani 1 1 d . . .
C12 C -0.5297(5) 0.18064(7) 0.7532(5) 0.0184(7) Uani 1 1 d . . .
H12 H -0.6254 0.1657 0.6955 0.022 Uiso 1 1 calc R . .
C16 C -0.2637(5) 0.04678(7) 0.3053(5) 0.0183(7) Uani 1 1 d . . .
C1 C -0.1364(5) 0.09292(7) 0.8659(5) 0.0171(7) Uani 1 1 d . . .
C13 C -0.7753(5) 0.22533(8) 0.6521(5) 0.0257(8) Uani 1 1 d . . .
H13A H -0.7978 0.2157 0.5241 0.039 Uiso 1 1 calc R . .
H13B H -0.7684 0.2486 0.6401 0.039 Uiso 1 1 calc R . .
H13C H -0.8884 0.2196 0.7282 0.039 Uiso 1 1 calc R . .
C4 C -0.2719(5) 0.03117(8) 0.7973(5) 0.0241(8) Uani 1 1 d . . .
H4 H -0.3139 0.0096 0.7768 0.029 Uiso 1 1 calc R . .
C5 C -0.0635(6) 0.03757(8) 0.8583(5) 0.0220(8) Uani 1 1 d . . .
H5 H 0.0298 0.0202 0.8748 0.026 Uiso 1 1 calc R . .
C6 C 0.0067(5) 0.06792(8) 0.8939(5) 0.0216(8) Uani 1 1 d . . .
H6 H 0.1460 0.0720 0.9356 0.026 Uiso 1 1 calc R . .
C2 C -0.3446(5) 0.08672(7) 0.8014(5) 0.0180(7) Uani 1 1 d . . .
C10 C -0.4317(5) 0.23388(8) 0.8400(5) 0.0219(8) Uani 1 1 d . . .
H10 H -0.4610 0.2561 0.8404 0.026 Uiso 1 1 calc R . .
C8 C -0.1972(5) 0.19104(8) 0.9260(5) 0.0192(7) Uani 1 1 d . . .
C7 C -0.3428(5) 0.16986(7) 0.8400(5) 0.0168(7) Uani 1 1 d . . .
C11 C -0.5768(5) 0.21306(7) 0.7504(5) 0.0201(7) Uani 1 1 d . . .
C3 C -0.4139(5) 0.05500(7) 0.7672(5) 0.0215(8) Uani 1 1 d . . .
H3 H -0.5525 0.0505 0.7253 0.026 Uiso 1 1 calc R . .
C9 C -0.2481(5) 0.22337(8) 0.9274(5) 0.0218(8) Uani 1 1 d . . .
H9 H -0.1552 0.2383 0.9893 0.026 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C14 1.347(3) . ?
F4 C17 1.346(4) . ?
F5 C18 1.353(3) . ?
F8 C21 1.347(3) . ?
F2 C15 1.338(3) . ?
F7 C20 1.339(3) . ?
F3 C16 1.349(3) . ?
F6 C19 1.344(3) . ?
C23 C22 1.428(4) . ?
C23 C17 1.415(4) . ?
C23 C18 1.407(4) . ?
C22 C21 1.416(4) . ?
C22 C14 1.419(4) . ?
C19 C20 1.397(4) . ?
C19 C18 1.367(4) . ?
C21 C20 1.357(4) . ?
C15 C14 1.361(4) . ?
C15 C16 1.406(4) . ?
N1 N2 1.344(4) . ?
N1 C1 1.351(4) . ?
N2 N3 1.337(4) . ?
N2 C7 1.438(4) . ?
O1 H1 0.8400 . ?
O1 C8 1.366(4) . ?
C17 C16 1.354(4) . ?
N3 C2 1.359(4) . ?
C12 H12 0.9500 . ?
C12 C7 1.395(4) . ?
C12 C11 1.391(4) . ?
C1 C6 1.408(4) . ?
C1 C2 1.425(5) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C13 C11 1.509(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.422(5) . ?
C4 C3 1.369(5) . ?
C5 H5 0.9500 . ?
C5 C6 1.366(4) . ?
C6 H6 0.9500 . ?
C2 C3 1.417(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.398(5) . ?
C10 C9 1.375(5) . ?
C8 C7 1.400(4) . ?
C8 C9 1.394(4) . ?
C3 H3 0.9500 . ?
C9 H9 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 C23 C22 117.7(3) . . ?
C18 C23 C22 118.5(3) . . ?
C18 C23 C17 123.8(3) . . ?
C21 C22 C23 118.0(3) . . ?
C21 C22 C14 123.2(3) . . ?
C14 C22 C23 118.8(3) . . ?
F6 C19 C20 119.4(3) . . ?
F6 C19 C18 120.9(3) . . ?
C18 C19 C20 119.7(3) . . ?
F8 C21 C22 120.0(3) . . ?
F8 C21 C20 118.5(3) . . ?
C20 C21 C22 121.5(3) . . ?
F2 C15 C14 121.1(3) . . ?
F2 C15 C16 119.7(3) . . ?
C14 C15 C16 119.3(3) . . ?
F1 C14 C22 120.5(3) . . ?
F1 C14 C15 117.9(3) . . ?
C15 C14 C22 121.6(3) . . ?
N2 N1 C1 103.0(3) . . ?
F7 C20 C19 119.0(3) . . ?
F7 C20 C21 120.4(3) . . ?
C21 C20 C19 120.6(3) . . ?
N1 N2 C7 120.9(3) . . ?
N3 N2 N1 117.4(2) . . ?
N3 N2 C7 121.7(3) . . ?
C8 O1 H1 109.5 . . ?
F4 C17 C23 120.4(3) . . ?
F4 C17 C16 118.1(3) . . ?
C16 C17 C23 121.6(3) . . ?
N2 N3 C2 102.3(2) . . ?
F5 C18 C23 120.7(3) . . ?
F5 C18 C19 117.6(3) . . ?
C19 C18 C23 121.7(3) . . ?
C7 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C7 120.5(3) . . ?
F3 C16 C15 118.0(3) . . ?
F3 C16 C17 120.9(3) . . ?
C17 C16 C15 121.1(3) . . ?
N1 C1 C6 130.5(3) . . ?
N1 C1 C2 108.3(3) . . ?
C6 C1 C2 121.2(3) . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
C3 C4 C5 122.2(3) . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 122.0(3) . . ?
C6 C5 H5 119.0 . . ?
C1 C6 H6 121.5 . . ?
C5 C6 C1 117.1(3) . . ?
C5 C6 H6 121.5 . . ?
N3 C2 C1 109.0(3) . . ?
N3 C2 C3 130.4(3) . . ?
C3 C2 C1 120.6(3) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C9 C10 C11 122.4(3) . . ?
O1 C8 C7 125.4(3) . . ?
O1 C8 C9 117.1(3) . . ?
C9 C8 C7 117.6(3) . . ?
C12 C7 N2 118.1(3) . . ?
C12 C7 C8 121.5(3) . . ?
C8 C7 N2 120.3(3) . . ?
C12 C11 C13 121.4(3) . . ?
C12 C11 C10 117.4(3) . . ?
C10 C11 C13 121.3(3) . . ?
C4 C3 C2 116.9(3) . . ?
C4 C3 H3 121.6 . . ?
C2 C3 H3 121.6 . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?

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
F4 C17 C16 F3 -0.3(5) . . . . ?
F4 C17 C16 C15 -178.4(3) . . . . ?
F8 C21 C20 F7 0.1(5) . . . . ?
F8 C21 C20 C19 178.7(3) . . . . ?
F2 C15 C14 F1 -2.0(5) . . . . ?
F2 C15 C14 C22 179.2(3) . . . . ?
F2 C15 C16 F3 1.9(5) . . . . ?
F2 C15 C16 C17 -179.9(3) . . . . ?
F6 C19 C20 F7 -0.7(5) . . . . ?
F6 C19 C20 C21 -179.3(3) . . . . ?
F6 C19 C18 F5 1.3(5) . . . . ?
F6 C19 C18 C23 -179.5(3) . . . . ?
C23 C22 C21 F8 -179.5(3) . . . . ?
C23 C22 C21 C20 0.4(5) . . . . ?
C23 C22 C14 F1 -178.4(3) . . . . ?
C23 C22 C14 C15 0.4(5) . . . . ?
C23 C17 C16 F3 179.1(3) . . . . ?
C23 C17 C16 C15 1.0(5) . . . . ?
C22 C23 C17 F4 177.7(3) . . . . ?
C22 C23 C17 C16 -1.7(5) . . . . ?
C22 C23 C18 F5 178.1(3) . . . . ?
C22 C23 C18 C19 -1.1(5) . . . . ?
C22 C21 C20 F7 -179.7(3) . . . . ?
C22 C21 C20 C19 -1.1(5) . . . . ?
C21 C22 C14 F1 1.4(5) . . . . ?
C21 C22 C14 C15 -179.9(3) . . . . ?
C14 C22 C21 F8 0.7(5) . . . . ?
C14 C22 C21 C20 -179.4(3) . . . . ?
C14 C15 C16 F3 -177.7(3) . . . . ?
C14 C15 C16 C17 0.5(5) . . . . ?
N1 N2 N3 C2 -0.6(4) . . . . ?
N1 N2 C7 C12 168.1(3) . . . . ?
N1 N2 C7 C8 -11.1(4) . . . . ?
N1 C1 C6 C5 -179.1(3) . . . . ?
N1 C1 C2 N3 -0.8(4) . . . . ?
N1 C1 C2 C3 -180.0(3) . . . . ?
C20 C19 C18 F5 -178.9(3) . . . . ?
C20 C19 C18 C23 0.3(5) . . . . ?
N2 N1 C1 C6 179.0(3) . . . . ?
N2 N1 C1 C2 0.4(3) . . . . ?
N2 N3 C2 C1 0.8(3) . . . . ?
N2 N3 C2 C3 179.9(3) . . . . ?
O1 C8 C7 N2 -0.2(5) . . . . ?
O1 C8 C7 C12 -179.4(3) . . . . ?
O1 C8 C9 C10 178.6(3) . . . . ?
C17 C23 C22 C21 -178.7(3) . . . . ?
C17 C23 C22 C14 1.0(4) . . . . ?
C17 C23 C18 F5 -2.5(5) . . . . ?
C17 C23 C18 C19 178.3(3) . . . . ?
N3 N2 C7 C12 -12.1(4) . . . . ?
N3 N2 C7 C8 168.7(3) . . . . ?
N3 C2 C3 C4 -179.5(3) . . . . ?
C18 C23 C22 C21 0.7(4) . . . . ?
C18 C23 C22 C14 -179.5(3) . . . . ?
C18 C23 C17 F4 -1.8(5) . . . . ?
C18 C23 C17 C16 178.8(3) . . . . ?
C18 C19 C20 F7 179.4(3) . . . . ?
C18 C19 C20 C21 0.8(5) . . . . ?
C16 C15 C14 F1 177.7(3) . . . . ?
C16 C15 C14 C22 -1.2(5) . . . . ?
C1 N1 N2 N3 0.1(4) . . . . ?
C1 N1 N2 C7 179.9(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C4 C5 C6 C1 -0.5(5) . . . . ?
C5 C4 C3 C2 -0.6(5) . . . . ?
C6 C1 C2 N3 -179.6(3) . . . . ?
C6 C1 C2 C3 1.3(5) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C7 N2 N3 C2 179.6(3) . . . . ?
C7 C12 C11 C13 178.1(3) . . . . ?
C7 C12 C11 C10 -1.0(5) . . . . ?
C7 C8 C9 C10 -2.6(5) . . . . ?
C11 C12 C7 N2 -179.4(3) . . . . ?
C11 C12 C7 C8 -0.2(5) . . . . ?
C11 C10 C9 C8 1.5(5) . . . . ?
C3 C4 C5 C6 1.2(5) . . . . ?
C9 C10 C11 C12 0.3(5) . . . . ?
C9 C10 C11 C13 -178.8(3) . . . . ?
C9 C8 C7 N2 -178.8(3) . . . . ?
C9 C8 C7 C12 2.0(5) . . . . ?

####################################################################### 
# 
# 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_exp_1960
_database_code_depnum_ccdc_archive 'CCDC 1454755'
_audit_update_record             
;
2016-02-19 deposited with the CCDC.
2016-11-14 downloaded from the CCDC.
;
_audit_creation_date             2014-03-05
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '2(C3 F2 I), 2(C13 H11 N3 O)'
_chemical_formula_sum            'C32 H22 F4 I2 N6 O2'
_chemical_formula_weight         852.36
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   15.842(8)
_cell_length_b                   5.6980(5)
_cell_length_c                   16.7517(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.72(2)
_cell_angle_gamma                90.00
_cell_volume                     1507.0(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2276
_cell_measurement_temperature    97.20(10)
_cell_measurement_theta_max      28.8620
_cell_measurement_theta_min      3.8870
_exptl_absorpt_coefficient_mu    2.154
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0553
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6391
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.40
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      97.20(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0971
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9971
_diffrn_measured_fraction_theta_max 0.8493
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    2.00   57.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335   37.0000   30.0000 55

#__ type_ start__ end____ width___ exp.time_
  2 omega  -21.00   23.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -13.4210  -99.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega  -36.00   46.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -19.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
  4 omega   -4.00   45.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -       18.7335  -99.0000   90.0000 49
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0222052000
_diffrn_orient_matrix_UB_12      0.1080483000
_diffrn_orient_matrix_UB_13      -0.0028518000
_diffrn_orient_matrix_UB_21      -0.0381102000
_diffrn_orient_matrix_UB_22      -0.0607448000
_diffrn_orient_matrix_UB_23      -0.0116385000
_diffrn_orient_matrix_UB_31      -0.0085658000
_diffrn_orient_matrix_UB_32      -0.0097379000
_diffrn_orient_matrix_UB_33      0.0407624000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2559
_reflns_number_total             2944
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0291P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0753
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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
I1 I 0.374363(15) 0.56420(4) 0.320370(13) 0.01947(10) Uani 1 1 d . . .
F1 F 0.50895(13) 0.1705(4) 0.38410(11) 0.0223(5) Uani 1 1 d . . .
O1 O 0.04853(16) 0.3077(4) 0.03403(13) 0.0180(5) Uani 1 1 d . . .
H1 H 0.0725 0.4301 0.0235 0.027 Uiso 1 1 calc R . .
N2 N 0.18015(19) 0.5525(5) 0.13443(17) 0.0118(6) Uani 1 1 d . . .
F2 F 0.39778(13) 0.8797(4) 0.47794(12) 0.0216(5) Uani 1 1 d . . .
N1 N 0.24125(18) 0.6577(5) 0.18074(16) 0.0140(6) Uani 1 1 d . . .
C6 C 0.1580(2) 0.2660(6) 0.23772(19) 0.0142(8) Uani 1 1 d . . .
H6 H 0.1980 0.3458 0.2713 0.017 Uiso 1 1 calc R . .
C4 C 0.0607(2) -0.0497(6) 0.2132(2) 0.0147(8) Uani 1 1 d . . .
H4 H 0.0353 -0.1858 0.2303 0.018 Uiso 1 1 calc R . .
C5 C 0.1206(2) 0.0642(6) 0.2650(2) 0.0145(8) Uani 1 1 d . . .
C2 C 0.0752(2) 0.2383(6) 0.10973(19) 0.0141(7) Uani 1 1 d . . .
C3 C 0.0382(2) 0.0340(6) 0.1374(2) 0.0159(8) Uani 1 1 d . . .
H3 H -0.0020 -0.0461 0.1042 0.019 Uiso 1 1 calc R . .
C1 C 0.1365(2) 0.3503(6) 0.1607(2) 0.0121(7) Uani 1 1 d . . .
N3 N 0.16036(18) 0.6477(5) 0.06215(16) 0.0127(6) Uani 1 1 d . . .
C7 C 0.1456(3) -0.0306(7) 0.3474(2) 0.0231(9) Uani 1 1 d . . .
H7A H 0.1994 -0.1085 0.3474 0.035 Uiso 1 1 calc R . .
H7B H 0.1036 -0.1402 0.3621 0.035 Uiso 1 1 calc R . .
H7C H 0.1499 0.0964 0.3851 0.035 Uiso 1 1 calc R . .
C15 C 0.4506(2) 0.5263(6) 0.4267(2) 0.0158(8) Uani 1 1 d . . .
C8 C 0.2636(2) 0.8394(6) 0.13480(19) 0.0121(7) Uani 1 1 d . . .
C12 C 0.3315(2) 1.1835(6) 0.0936(2) 0.0163(8) Uani 1 1 d . . .
H12 H 0.3706 1.3042 0.1029 0.020 Uiso 1 1 calc R . .
C13 C 0.3239(2) 1.0178(6) 0.1519(2) 0.0164(8) Uani 1 1 d . . .
H13 H 0.3570 1.0229 0.2004 0.020 Uiso 1 1 calc R . .
C9 C 0.2139(2) 0.8313(6) 0.06135(19) 0.0132(8) Uani 1 1 d . . .
C11 C 0.2812(2) 1.1757(6) 0.0193(2) 0.0169(8) Uani 1 1 d . . .
H11 H 0.2884 1.2922 -0.0185 0.020 Uiso 1 1 calc R . .
C10 C 0.2228(2) 1.0038(6) 0.0013(2) 0.0174(8) Uani 1 1 d . . .
H10 H 0.1905 0.9996 -0.0476 0.021 Uiso 1 1 calc R . .
C14 C 0.5031(2) 0.3353(6) 0.4409(2) 0.0142(8) Uani 1 1 d . . .
C16 C 0.4487(2) 0.6910(6) 0.48750(19) 0.0146(8) 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
I1 C15 2.078(4) . ?
F1 C14 1.346(4) . ?
O1 H1 0.8200 . ?
O1 C2 1.362(4) . ?
N2 N1 1.332(4) . ?
N2 C1 1.432(4) . ?
N2 N3 1.340(4) . ?
F2 C16 1.346(4) . ?
N1 C8 1.354(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.388(5) . ?
C6 C1 1.392(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(5) . ?
C4 C3 1.375(5) . ?
C5 C7 1.505(5) . ?
C2 C3 1.399(5) . ?
C2 C1 1.395(5) . ?
C3 H3 0.9300 . ?
N3 C9 1.348(4) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C15 C14 1.379(5) . ?
C15 C16 1.388(5) . ?
C8 C13 1.408(5) . ?
C8 C9 1.406(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.370(5) . ?
C12 C11 1.423(5) . ?
C13 H13 0.9300 . ?
C9 C10 1.421(5) . ?
C11 H11 0.9300 . ?
C11 C10 1.364(5) . ?
C10 H10 0.9300 . ?
C14 C16 1.376(5) 3_666 ?
C16 C14 1.376(5) 3_666 ?

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
C2 O1 H1 109.5 . . ?
N1 N2 C1 121.9(3) . . ?
N1 N2 N3 116.7(3) . . ?
N3 N2 C1 121.4(3) . . ?
N2 N1 C8 103.0(3) . . ?
C5 C6 H6 119.6 . . ?
C5 C6 C1 120.8(3) . . ?
C1 C6 H6 119.6 . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C3 C4 C5 121.7(3) . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 C7 120.8(3) . . ?
C4 C5 C7 121.3(3) . . ?
O1 C2 C3 116.4(3) . . ?
O1 C2 C1 125.7(3) . . ?
C1 C2 C3 117.8(3) . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C6 C1 N2 118.4(3) . . ?
C6 C1 C2 121.0(3) . . ?
C2 C1 N2 120.6(3) . . ?
N2 N3 C9 102.9(3) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C14 C15 I1 122.0(3) . . ?
C14 C15 C16 117.1(3) . . ?
C16 C15 I1 120.9(3) . . ?
N1 C8 C13 129.9(3) . . ?
N1 C8 C9 108.6(3) . . ?
C9 C8 C13 121.5(3) . . ?
C13 C12 H12 119.1 . . ?
C13 C12 C11 121.8(3) . . ?
C11 C12 H12 119.1 . . ?
C8 C13 H13 121.6 . . ?
C12 C13 C8 116.8(3) . . ?
C12 C13 H13 121.6 . . ?
N3 C9 C8 108.9(3) . . ?
N3 C9 C10 130.0(3) . . ?
C8 C9 C10 121.1(3) . . ?
C12 C11 H11 118.8 . . ?
C10 C11 C12 122.4(3) . . ?
C10 C11 H11 118.8 . . ?
C9 C10 H10 121.8 . . ?
C11 C10 C9 116.4(3) . . ?
C11 C10 H10 121.8 . . ?
F1 C14 C15 120.3(3) . . ?
F1 C14 C16 118.4(3) . 3_666 ?
C16 C14 C15 121.4(3) 3_666 . ?
F2 C16 C15 120.1(3) . . ?
F2 C16 C14 118.4(3) . 3_666 ?
C14 C16 C15 121.5(3) 3_666 . ?

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
I1 C15 C14 F1 2.8(4) . . . . ?
I1 C15 C14 C16 -178.0(2) . . . 3_666 ?
I1 C15 C16 F2 -0.7(4) . . . . ?
I1 C15 C16 C14 178.1(2) . . . 3_666 ?
O1 C2 C3 C4 -179.7(3) . . . . ?
O1 C2 C1 N2 -2.3(5) . . . . ?
O1 C2 C1 C6 179.0(3) . . . . ?
N2 N1 C8 C13 178.4(3) . . . . ?
N2 N1 C8 C9 -0.6(3) . . . . ?
N2 N3 C9 C8 -0.6(3) . . . . ?
N2 N3 C9 C10 -178.7(3) . . . . ?
N1 N2 C1 C6 1.3(5) . . . . ?
N1 N2 C1 C2 -177.4(3) . . . . ?
N1 N2 N3 C9 0.3(4) . . . . ?
N1 C8 C13 C12 -178.6(3) . . . . ?
N1 C8 C9 N3 0.8(4) . . . . ?
N1 C8 C9 C10 179.1(3) . . . . ?
C5 C6 C1 N2 -176.9(3) . . . . ?
C5 C6 C1 C2 1.8(5) . . . . ?
C5 C4 C3 C2 0.0(5) . . . . ?
C3 C4 C5 C6 -0.5(5) . . . . ?
C3 C4 C5 C7 -179.2(3) . . . . ?
C3 C2 C1 N2 176.5(3) . . . . ?
C3 C2 C1 C6 -2.2(5) . . . . ?
C1 N2 N1 C8 -178.7(3) . . . . ?
C1 N2 N3 C9 179.2(3) . . . . ?
C1 C6 C5 C4 -0.4(5) . . . . ?
C1 C6 C5 C7 178.3(3) . . . . ?
C1 C2 C3 C4 1.3(5) . . . . ?
N3 N2 N1 C8 0.2(4) . . . . ?
N3 N2 C1 C6 -177.5(3) . . . . ?
N3 N2 C1 C2 3.7(5) . . . . ?
N3 C9 C10 C11 177.5(3) . . . . ?
C8 C9 C10 C11 -0.4(5) . . . . ?
C12 C11 C10 C9 0.5(5) . . . . ?
C13 C8 C9 N3 -178.3(3) . . . . ?
C13 C8 C9 C10 0.0(5) . . . . ?
C13 C12 C11 C10 -0.2(5) . . . . ?
C9 C8 C13 C12 0.3(5) . . . . ?
C11 C12 C13 C8 -0.2(5) . . . . ?
C14 C15 C16 F2 -178.9(3) . . . . ?
C14 C15 C16 C14 -0.2(5) . . . 3_666 ?
C16 C15 C14 F1 -179.0(3) . . . . ?
C16 C15 C14 C16 0.2(5) . . . 3_666 ?

