# Electronic Supplementary Material (ESI) for RSC Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1021573'
_audit_update_record             
;
2014-08-28 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H32 F10 N6 O2 Zn'
_chemical_formula_weight         1004.18

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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   23.891(4)
_cell_length_b                   13.986(4)
_cell_length_c                   14.697(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.084(15)
_cell_angle_gamma                90
_cell_volume                     4742(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6532
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      24.6

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             2040
_exptl_transmission_factor_min   0.78
_exptl_transmission_factor_max   0.88
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.603
_shelx_estimated_absorpt_T_min   0.840
_shelx_estimated_absorpt_T_max   0.889
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14729
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.371
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             4170
_reflns_number_gt                2810
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/6 (Sheldrick, 2014)'
_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)+(0.1015P)²+1.2970P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'direct methods'
_atom_sites_solution_secondary   fourier
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4170
_refine_ls_number_parameters     361
_refine_ls_number_restraints     393
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1754
_refine_ls_wR_factor_gt          0.1472
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.034
_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
C1 C 0.36965(18) 0.3076(3) 0.4786(3) 0.0479(9) Uani 1 1 d . . . . .
C2 C 0.3978(2) 0.3678(3) 0.4241(3) 0.0695(13) Uani 1 1 d . . . . .
H2 H 0.4374 0.3706 0.4288 0.083 Uiso 1 1 calc R U . . .
C3 C 0.3565(2) 0.4185(3) 0.3660(3) 0.0637(12) Uani 1 1 d . . . . .
H3 H 0.3619 0.4631 0.3221 0.076 Uiso 1 1 calc R U . . .
C4 C 0.30169(17) 0.3920(2) 0.3833(2) 0.0411(9) Uani 1 1 d . . . . .
C6 C 0.19325(17) 0.3974(2) 0.3473(2) 0.0377(8) Uani 1 1 d . . . . .
C7 C 0.13768(19) 0.4365(3) 0.3007(3) 0.0562(11) Uani 1 1 d . . . . .
H7 H 0.1306 0.4850 0.2559 0.067 Uiso 1 1 calc R U . . .
C8 C 0.0979(2) 0.3907(3) 0.3333(3) 0.0677(12) Uani 1 1 d . . . . .
H8 H 0.0581 0.4011 0.3154 0.081 Uiso 1 1 calc R U . . .
C9 C 0.12824(18) 0.3220(2) 0.4013(2) 0.0464(9) Uani 1 1 d . . . . .
C5 C 0.24668(17) 0.4269(2) 0.3348(2) 0.0394(9) Uani 1 1 d D . . . .
C11 C 0.2456(10) 0.4969(7) 0.2560(9) 0.037(3) Uani 0.742(17) 1 d D U P A 1
C12 C 0.2692(5) 0.5906(6) 0.2814(5) 0.053(2) Uani 0.742(17) 1 d . U P A 1
H12 H 0.2836 0.6081 0.3442 0.063 Uiso 0.742(17) 1 calc R U P A 1
C13 C 0.2697(5) 0.6538(6) 0.2096(6) 0.055(2) Uani 0.742(17) 1 d . U P A 1
H13 H 0.2867 0.7135 0.2249 0.066 Uiso 0.742(17) 1 calc R U P A 1
N3 N 0.2459(7) 0.6316(12) 0.1145(10) 0.040(2) Uani 0.742(17) 1 d . U P A 1
C14 C 0.2237(5) 0.5472(7) 0.0977(6) 0.054(2) Uani 0.742(17) 1 d . U P A 1
H14 H 0.2073 0.5309 0.0351 0.065 Uiso 0.742(17) 1 calc R U P A 1
C15 C 0.2222(5) 0.4796(6) 0.1646(5) 0.051(2) Uani 0.742(17) 1 d . U P A 1
H15 H 0.2047 0.4208 0.1461 0.061 Uiso 0.742(17) 1 calc R U P A 1
C11' C 0.246(3) 0.510(2) 0.269(3) 0.040(5) Uani 0.258(17) 1 d D U P A 2
C12' C 0.2399(13) 0.5943(18) 0.2707(17) 0.051(4) Uani 0.258(17) 1 d . U P A 2
H12' H 0.2331 0.6202 0.3251 0.061 Uiso 0.258(17) 1 calc R U P A 2
C13' C 0.2420(13) 0.6560(18) 0.2010(19) 0.050(4) Uani 0.258(17) 1 d . U P A 2
H13' H 0.2325 0.7189 0.2111 0.060 Uiso 0.258(17) 1 calc R U P A 2
N3' N 0.254(2) 0.642(4) 0.130(3) 0.042(5) Uani 0.258(17) 1 d . U P A 2
C14' C 0.2506(13) 0.545(2) 0.106(2) 0.052(4) Uani 0.258(17) 1 d . U P A 2
H14' H 0.2481 0.5261 0.0443 0.062 Uiso 0.258(17) 1 calc R U P A 2
C15' C 0.2510(13) 0.4776(17) 0.1736(17) 0.050(4) Uani 0.258(17) 1 d . U P A 2
H15' H 0.2545 0.4130 0.1612 0.061 Uiso 0.258(17) 1 calc R U P A 2
C10 C 0.39759(19) 0.2402(3) 0.5455(3) 0.0539(10) Uani 1 1 d D . . . .
C16 C 0.4642 0.2408 0.5707 0.061 Uani 0.7236 1 d D U P B 3
C17 C 0.4976 0.3128 0.6236 0.074 Uani 0.7236 1 d D U P B 3
C18 C 0.5577 0.3080 0.6450 0.087 Uani 0.7236 1 d D U P B 3
C19 C 0.5845 0.2311 0.6135 0.100 Uani 0.7236 1 d D U P B 3
C20 C 0.5511 0.1591 0.5606 0.099 Uani 0.7236 1 d D U P B 3
C21 C 0.4910 0.1640 0.5392 0.084 Uani 0.7236 1 d D U P B 3
F1 F 0.47331(19) 0.3844(3) 0.6534(3) 0.0952(15) Uani 0.724(5) 1 d D U P B 3
F2 F 0.5894(2) 0.3747(4) 0.6947(4) 0.130(2) Uani 0.724(5) 1 d D U P B 3
F3 F 0.64094(19) 0.2270(4) 0.6317(5) 0.127(2) Uani 0.724(5) 1 d D U P B 3
F4 F 0.5770(3) 0.0888(4) 0.5294(6) 0.158(3) Uani 0.724(5) 1 d D U P B 3
F5 F 0.4614(2) 0.0968(3) 0.4897(5) 0.120(2) Uani 0.724(5) 1 d D U P B 3
C16' C 0.4556 0.2004 0.5246 0.080 Uani 0.2759 1 d D U P B 4
C17' C 0.5045 0.2334 0.5908 0.093 Uani 0.2759 1 d D U P B 4
C18' C 0.5594 0.2081 0.5835 0.120 Uani 0.2759 1 d D U P B 4
C19' C 0.5654 0.1499 0.5100 0.131 Uani 0.2759 1 d D U P B 4
C20' C 0.5165 0.1168 0.4438 0.120 Uani 0.2759 1 d D U P B 4
C21' C 0.4616 0.1421 0.4512 0.091 Uani 0.2759 1 d D U P B 4
F1' F 0.4967(7) 0.2962(12) 0.6512(10) 0.166(8) Uani 0.276(5) 1 d D U P B 4
F2' F 0.5950(9) 0.2636(13) 0.6422(13) 0.218(10) Uani 0.276(5) 1 d D U P B 4
F3' F 0.6188(7) 0.1281(18) 0.514(2) 0.239(10) Uani 0.276(5) 1 d D U P B 4
F4' F 0.5261(9) 0.0625(14) 0.3777(15) 0.242(10) Uani 0.276(5) 1 d D U P B 4
F5' F 0.4171(6) 0.1069(11) 0.3903(12) 0.169(8) Uani 0.276(5) 1 d D U P B 4
N1 N 0.31129(14) 0.32432(18) 0.45306(18) 0.0396(7) Uani 1 1 d . . . . .
N2 N 0.18610(13) 0.32719(17) 0.40804(17) 0.0352(7) Uani 1 1 d . . . . .
Zn1 Zn 0.2500 0.2500 0.5000 0.0378(2) Uani 1 2 d S . P . .
C22 C 0.6476(18) 0.394(2) 0.425(3) 0.573(12) Uani 1 1 d D U . . .
H22A H 0.6530 0.4149 0.4893 0.687 Uiso 1 1 calc R U . . .
H22B H 0.6635 0.4422 0.3915 0.687 Uiso 1 1 calc R U . . .
C23 C 0.6810(10) 0.296(3) 0.424(3) 0.582(12) Uani 1 1 d D U . . .
H23A H 0.7181 0.3064 0.4104 0.698 Uiso 1 1 calc R U . . .
H23B H 0.6869 0.2626 0.4834 0.698 Uiso 1 1 calc R U . . .
C24 C 0.638(2) 0.2401(17) 0.342(3) 0.592(12) Uani 1 1 d D U . . .
H24A H 0.6491 0.2477 0.2830 0.710 Uiso 1 1 calc R U . . .
H24B H 0.6379 0.1725 0.3563 0.710 Uiso 1 1 calc R U . . .
C25 C 0.5777(13) 0.285(3) 0.334(3) 0.589(12) Uani 1 1 d D U . . .
H25A H 0.5566 0.2912 0.2682 0.706 Uiso 1 1 calc R U . . .
H25B H 0.5554 0.2442 0.3648 0.706 Uiso 1 1 calc R U . . .
O1 O 0.5856(15) 0.382(2) 0.380(2) 0.588(11) Uani 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.367(5) . ?
C1 C10 1.399(5) . ?
C1 C2 1.444(5) . ?
C2 C3 1.330(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.445(6) . ?
C3 H3 0.9300 . ?
C4 N1 1.371(4) . ?
C4 C5 1.409(5) . ?
C6 N2 1.368(4) . ?
C6 C5 1.398(5) . ?
C6 C7 1.434(5) . ?
C7 C8 1.333(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.439(5) . ?
C8 H8 0.9300 . ?
C9 N2 1.362(5) . ?
C9 C10 1.414(5) 7_556 ?
C5 C11 1.512(6) . ?
C5 C11' 1.513(10) . ?
C11 C15 1.336(16) . ?
C11 C12 1.438(17) . ?
C12 C13 1.379(10) . ?
C12 H12 0.9300 . ?
C13 N3 1.400(17) . ?
C13 H13 0.9300 . ?
N3 C14 1.292(17) . ?
N3 Zn1 2.381(17) 4 ?
C14 C15 1.371(11) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C11' C12' 1.18(4) . ?
C11' C15' 1.51(5) . ?
C12' C13' 1.35(3) . ?
C12' H12' 0.9300 . ?
C13' N3' 1.17(6) . ?
C13' H13' 0.9300 . ?
N3' C14' 1.41(5) . ?
N3' Zn1 2.42(5) 4 ?
C14' C15' 1.37(3) . ?
C14' H14' 0.9300 . ?
C15' H15' 0.9300 . ?
C10 C9 1.414(5) 7_556 ?
C10 C16 1.537(4) . ?
C10 C16' 1.595(4) . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 F1 1.289(4) . ?
C17 C18 1.3900 . ?
C18 F2 1.300(4) . ?
C18 C19 1.3900 . ?
C19 F3 1.307(4) . ?
C19 C20 1.3900 . ?
C20 F4 1.308(5) . ?
C20 C21 1.3900 . ?
C21 F5 1.282(4) . ?
C16' C17' 1.3900 . ?
C16' C21' 1.3900 . ?
C17' F1' 1.296(11) . ?
C17' C18' 1.3900 . ?
C18' F2' 1.300(12) . ?
C18' C19' 1.3900 . ?
C19' F3' 1.297(11) . ?
C19' C20' 1.3900 . ?
C20' F4' 1.301(11) . ?
C20' C21' 1.3900 . ?
C21' F5' 1.296(11) . ?
N1 Zn1 2.056(3) . ?
N2 Zn1 2.061(3) . ?
Zn1 N1 2.056(3) 7_556 ?
Zn1 N2 2.061(3) 7_556 ?
Zn1 N3 2.381(17) 6_566 ?
Zn1 N3 2.381(17) 4_545 ?
Zn1 N3' 2.42(5) 4_545 ?
Zn1 N3' 2.42(5) 6_566 ?
C22 O1 1.463(17) . ?
C22 C23 1.582(17) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.576(17) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.551(17) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 O1 1.511(16) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?

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
N1 C1 C10 125.1(3) . . ?
N1 C1 C2 109.7(3) . . ?
C10 C1 C2 125.2(4) . . ?
C3 C2 C1 107.0(4) . . ?
C3 C2 H2 126.5 . . ?
C1 C2 H2 126.5 . . ?
C2 C3 C4 107.8(3) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
N1 C4 C5 124.7(3) . . ?
N1 C4 C3 109.0(3) . . ?
C5 C4 C3 126.2(3) . . ?
N2 C6 C5 124.8(3) . . ?
N2 C6 C7 109.1(3) . . ?
C5 C6 C7 126.1(3) . . ?
C8 C7 C6 107.6(3) . . ?
C8 C7 H7 126.2 . . ?
C6 C7 H7 126.2 . . ?
C7 C8 C9 107.1(4) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C10 125.0(3) . 7_556 ?
N2 C9 C8 109.4(3) . . ?
C10 C9 C8 125.6(4) 7_556 . ?
C6 C5 C4 126.5(3) . . ?
C6 C5 C11 117.2(9) . . ?
C4 C5 C11 116.0(9) . . ?
C6 C5 C11' 117(3) . . ?
C4 C5 C11' 117(3) . . ?
C15 C11 C12 117.4(6) . . ?
C15 C11 C5 124.9(10) . . ?
C12 C11 C5 117.6(11) . . ?
C13 C12 C11 117.8(8) . . ?
C13 C12 H12 121.1 . . ?
C11 C12 H12 121.1 . . ?
C12 C13 N3 122.7(10) . . ?
C12 C13 H13 118.7 . . ?
N3 C13 H13 118.7 . . ?
C14 N3 C13 115.7(13) . . ?
C14 N3 Zn1 126.3(8) . 4 ?
C13 N3 Zn1 118.1(10) . 4 ?
N3 C14 C15 125.4(9) . . ?
N3 C14 H14 117.3 . . ?
C15 C14 H14 117.3 . . ?
C11 C15 C14 120.9(7) . . ?
C11 C15 H15 119.5 . . ?
C14 C15 H15 119.5 . . ?
C12' C11' C15' 111.0(19) . . ?
C12' C11' C5 137(4) . . ?
C15' C11' C5 112(3) . . ?
C11' C12' C13' 126(3) . . ?
C11' C12' H12' 116.9 . . ?
C13' C12' H12' 116.9 . . ?
N3' C13' C12' 130(4) . . ?
N3' C13' H13' 115.1 . . ?
C12' C13' H13' 115.1 . . ?
C13' N3' C14' 112(4) . . ?
C13' N3' Zn1 130(4) . 4 ?
C14' N3' Zn1 115(3) . 4 ?
C15' C14' N3' 120(3) . . ?
C15' C14' H14' 120.2 . . ?
N3' C14' H14' 120.2 . . ?
C14' C15' C11' 119(2) . . ?
C14' C15' H15' 120.7 . . ?
C11' C15' H15' 120.7 . . ?
C1 C10 C9 127.3(4) . 7_556 ?
C1 C10 C16 116.1(3) . . ?
C9 C10 C16 116.3(3) 7_556 . ?
C1 C10 C16' 112.3(3) . . ?
C9 C10 C16' 114.7(3) 7_556 . ?
C17 C16 C21 120.0 . . ?
C17 C16 C10 123.12(15) . . ?
C21 C16 C10 116.87(15) . . ?
F1 C17 C18 119.40(19) . . ?
F1 C17 C16 120.60(19) . . ?
C18 C17 C16 120.0 . . ?
F2 C18 C17 120.6(3) . . ?
F2 C18 C19 119.4(3) . . ?
C17 C18 C19 120.0 . . ?
F3 C19 C20 119.6(3) . . ?
F3 C19 C18 120.4(3) . . ?
C20 C19 C18 120.0 . . ?
F4 C20 C19 119.1(3) . . ?
F4 C20 C21 120.9(3) . . ?
C19 C20 C21 120.0 . . ?
F5 C21 C20 118.5(2) . . ?
F5 C21 C16 121.5(2) . . ?
C20 C21 C16 120.0 . . ?
C17' C16' C21' 120.0 . . ?
C17' C16' C10 111.30(16) . . ?
C21' C16' C10 128.68(16) . . ?
F1' C17' C18' 122.1(7) . . ?
F1' C17' C16' 117.4(7) . . ?
C18' C17' C16' 120.0 . . ?
F2' C18' C17' 105.4(12) . . ?
F2' C18' C19' 133.1(13) . . ?
C17' C18' C19' 120.0 . . ?
F3' C19' C18' 113.6(15) . . ?
F3' C19' C20' 126.3(15) . . ?
C18' C19' C20' 120.0 . . ?
F4' C20' C21' 124.0(10) . . ?
F4' C20' C19' 116.0(10) . . ?
C21' C20' C19' 120.0 . . ?
F5' C21' C20' 118.2(6) . . ?
F5' C21' C16' 121.8(6) . . ?
C20' C21' C16' 120.0 . . ?
C1 N1 C4 106.5(3) . . ?
C1 N1 Zn1 125.9(2) . . ?
C4 N1 Zn1 127.2(3) . . ?
C9 N2 C6 106.7(3) . . ?
C9 N2 Zn1 125.7(2) . . ?
C6 N2 Zn1 127.4(3) . . ?
N1 Zn1 N1 180.0 . 7_556 ?
N1 Zn1 N2 89.18(11) . . ?
N1 Zn1 N2 90.82(11) 7_556 . ?
N1 Zn1 N2 90.82(11) . 7_556 ?
N1 Zn1 N2 89.18(11) 7_556 7_556 ?
N2 Zn1 N2 180.00(11) . 7_556 ?
N1 Zn1 N3 92.8(5) . 6_566 ?
N1 Zn1 N3 87.2(5) 7_556 6_566 ?
N2 Zn1 N3 86.5(3) . 6_566 ?
N2 Zn1 N3 93.5(3) 7_556 6_566 ?
N1 Zn1 N3 87.2(5) . 4_545 ?
N1 Zn1 N3 92.8(5) 7_556 4_545 ?
N2 Zn1 N3 93.5(3) . 4_545 ?
N2 Zn1 N3 86.5(3) 7_556 4_545 ?
N3 Zn1 N3 180.0 6_566 4_545 ?
N1 Zn1 N3' 86.2(13) . 4_545 ?
N1 Zn1 N3' 93.8(13) 7_556 4_545 ?
N2 Zn1 N3' 86.5(10) . 4_545 ?
N2 Zn1 N3' 93.5(10) 7_556 4_545 ?
N1 Zn1 N3' 93.8(13) . 6_566 ?
N1 Zn1 N3' 86.2(13) 7_556 6_566 ?
N2 Zn1 N3' 93.5(10) . 6_566 ?
N2 Zn1 N3' 86.5(10) 7_556 6_566 ?
N3' Zn1 N3' 180.0 4_545 6_566 ?
O1 C22 C23 110.9(12) . . ?
O1 C22 H22A 109.5 . . ?
C23 C22 H22A 109.5 . . ?
O1 C22 H22B 109.5 . . ?
C23 C22 H22B 109.5 . . ?
H22A C22 H22B 108.1 . . ?
C24 C23 C22 101.9(11) . . ?
C24 C23 H23A 111.4 . . ?
C22 C23 H23A 111.4 . . ?
C24 C23 H23B 111.4 . . ?
C22 C23 H23B 111.4 . . ?
H23A C23 H23B 109.2 . . ?
C25 C24 C23 105.1(12) . . ?
C25 C24 H24A 110.7 . . ?
C23 C24 H24A 110.7 . . ?
C25 C24 H24B 110.7 . . ?
C23 C24 H24B 110.7 . . ?
H24A C24 H24B 108.8 . . ?
O1 C25 C24 109.0(11) . . ?
O1 C25 H25A 109.9 . . ?
C24 C25 H25A 109.9 . . ?
O1 C25 H25B 109.9 . . ?
C24 C25 H25B 109.9 . . ?
H25A C25 H25B 108.3 . . ?
C22 O1 C25 107.1(10) . . ?

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
N1 C1 C2 C3 -0.9(5) . . . . ?
C10 C1 C2 C3 177.3(4) . . . . ?
C1 C2 C3 C4 0.5(5) . . . . ?
C2 C3 C4 N1 0.0(5) . . . . ?
C2 C3 C4 C5 -178.0(4) . . . . ?
N2 C6 C7 C8 0.2(4) . . . . ?
C5 C6 C7 C8 -178.6(4) . . . . ?
C6 C7 C8 C9 0.2(5) . . . . ?
C7 C8 C9 N2 -0.5(5) . . . . ?
C7 C8 C9 C10 178.5(4) . . . 7_556 ?
N2 C6 C5 C4 -1.7(5) . . . . ?
C7 C6 C5 C4 176.9(3) . . . . ?
N2 C6 C5 C11 172.6(6) . . . . ?
C7 C6 C5 C11 -8.8(8) . . . . ?
N2 C6 C5 C11' -176(2) . . . . ?
C7 C6 C5 C11' 3(2) . . . . ?
N1 C4 C5 C6 -1.8(5) . . . . ?
C3 C4 C5 C6 175.9(4) . . . . ?
N1 C4 C5 C11 -176.2(6) . . . . ?
C3 C4 C5 C11 1.5(8) . . . . ?
N1 C4 C5 C11' 172(2) . . . . ?
C3 C4 C5 C11' -10(2) . . . . ?
C6 C5 C11 C15 -62(2) . . . . ?
C4 C5 C11 C15 112.8(18) . . . . ?
C6 C5 C11 C12 114.9(14) . . . . ?
C4 C5 C11 C12 -70.2(15) . . . . ?
C15 C11 C12 C13 -4(2) . . . . ?
C5 C11 C12 C13 178.3(11) . . . . ?
C11 C12 C13 N3 3.2(17) . . . . ?
C12 C13 N3 C14 -1(2) . . . . ?
C12 C13 N3 Zn1 179.5(7) . . . 4 ?
C13 N3 C14 C15 0(2) . . . . ?
Zn1 N3 C14 C15 179.3(8) 4 . . . ?
C12 C11 C15 C14 4(2) . . . . ?
C5 C11 C15 C14 -179.5(12) . . . . ?
N3 C14 C15 C11 -1.1(19) . . . . ?
C6 C5 C11' C12' 75(9) . . . . ?
C4 C5 C11' C12' -100(9) . . . . ?
C6 C5 C11' C15' -102(4) . . . . ?
C4 C5 C11' C15' 84(4) . . . . ?
C15' C11' C12' C13' -5(8) . . . . ?
C5 C11' C12' C13' 178(5) . . . . ?
C11' C12' C13' N3' -6(7) . . . . ?
C12' C13' N3' C14' 18(6) . . . . ?
C12' C13' N3' Zn1 174(2) . . . 4 ?
C13' N3' C14' C15' -18(5) . . . . ?
Zn1 N3' C14' C15' -178(2) 4 . . . ?
N3' C14' C15' C11' 9(5) . . . . ?
C12' C11' C15' C14' 2(7) . . . . ?
C5 C11' C15' C14' 180(3) . . . . ?
N1 C1 C10 C9 -0.2(7) . . . 7_556 ?
C2 C1 C10 C9 -178.2(4) . . . 7_556 ?
N1 C1 C10 C16 -173.8(3) . . . . ?
C2 C1 C10 C16 8.2(6) . . . . ?
N1 C1 C10 C16' 151.3(3) . . . . ?
C2 C1 C10 C16' -26.7(5) . . . . ?
C1 C10 C16 C17 71.7(4) . . . . ?
C9 C10 C16 C17 -102.6(3) 7_556 . . . ?
C1 C10 C16 C21 -109.3(3) . . . . ?
C9 C10 C16 C21 76.4(4) 7_556 . . . ?
C21 C16 C17 F1 -179.9(3) . . . . ?
C10 C16 C17 F1 -0.8(3) . . . . ?
C21 C16 C17 C18 0.0 . . . . ?
C10 C16 C17 C18 179.01(17) . . . . ?
F1 C17 C18 F2 0.1(4) . . . . ?
C16 C17 C18 F2 -179.7(3) . . . . ?
F1 C17 C18 C19 179.9(3) . . . . ?
C16 C17 C18 C19 0.0 . . . . ?
F2 C18 C19 F3 -1.7(4) . . . . ?
C17 C18 C19 F3 178.6(3) . . . . ?
F2 C18 C19 C20 179.7(3) . . . . ?
C17 C18 C19 C20 0.0 . . . . ?
F3 C19 C20 F4 -0.5(5) . . . . ?
C18 C19 C20 F4 178.1(4) . . . . ?
F3 C19 C20 C21 -178.6(3) . . . . ?
C18 C19 C20 C21 0.0 . . . . ?
F4 C20 C21 F5 1.3(5) . . . . ?
C19 C20 C21 F5 179.4(3) . . . . ?
F4 C20 C21 C16 -178.1(4) . . . . ?
C19 C20 C21 C16 0.0 . . . . ?
C17 C16 C21 F5 -179.4(3) . . . . ?
C10 C16 C21 F5 1.5(4) . . . . ?
C17 C16 C21 C20 0.0 . . . . ?
C10 C16 C21 C20 -179.07(16) . . . . ?
C1 C10 C16' C17' 109.7(3) . . . . ?
C9 C10 C16' C17' -95.1(3) 7_556 . . . ?
C1 C10 C16' C21' -68.8(3) . . . . ?
C9 C10 C16' C21' 86.4(3) 7_556 . . . ?
C21' C16' C17' F1' 172.2(9) . . . . ?
C10 C16' C17' F1' -6.4(9) . . . . ?
C21' C16' C17' C18' 0.0 . . . . ?
C10 C16' C17' C18' -178.64(14) . . . . ?
F1' C17' C18' F2' -4.0(13) . . . . ?
C16' C17' C18' F2' 167.8(9) . . . . ?
F1' C17' C18' C19' -171.8(10) . . . . ?
C16' C17' C18' C19' 0.0 . . . . ?
F2' C18' C19' F3' 19.4(15) . . . . ?
C17' C18' C19' F3' -176.8(11) . . . . ?
F2' C18' C19' C20' -163.8(11) . . . . ?
C17' C18' C19' C20' 0.0 . . . . ?
F3' C19' C20' F4' -3.4(17) . . . . ?
C18' C19' C20' F4' -179.8(12) . . . . ?
F3' C19' C20' C21' 176.3(13) . . . . ?
C18' C19' C20' C21' 0.0 . . . . ?
F4' C20' C21' F5' 2.4(16) . . . . ?
C19' C20' C21' F5' -177.4(10) . . . . ?
F4' C20' C21' C16' 179.7(13) . . . . ?
C19' C20' C21' C16' 0.0 . . . . ?
C17' C16' C21' F5' 177.3(10) . . . . ?
C10 C16' C21' F5' -4.3(10) . . . . ?
C17' C16' C21' C20' 0.0 . . . . ?
C10 C16' C21' C20' 178.38(16) . . . . ?
C10 C1 N1 C4 -177.4(4) . . . . ?
C2 C1 N1 C4 0.9(4) . . . . ?
C10 C1 N1 Zn1 -3.9(5) . . . . ?
C2 C1 N1 Zn1 174.3(3) . . . . ?
C5 C4 N1 C1 177.5(3) . . . . ?
C3 C4 N1 C1 -0.6(4) . . . . ?
C5 C4 N1 Zn1 4.2(5) . . . . ?
C3 C4 N1 Zn1 -173.9(3) . . . . ?
C10 C9 N2 C6 -178.3(4) 7_556 . . . ?
C8 C9 N2 C6 0.6(4) . . . . ?
C10 C9 N2 Zn1 -2.4(5) 7_556 . . . ?
C8 C9 N2 Zn1 176.5(3) . . . . ?
C5 C6 N2 C9 178.3(3) . . . . ?
C7 C6 N2 C9 -0.5(4) . . . . ?
C5 C6 N2 Zn1 2.5(4) . . . . ?
C7 C6 N2 Zn1 -176.3(2) . . . . ?
O1 C22 C23 C24 21(5) . . . . ?
C22 C23 C24 C25 -24(4) . . . . ?
C23 C24 C25 O1 20(5) . . . . ?
C23 C22 O1 C25 -10(5) . . . . ?
C24 C25 O1 C22 -6(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
C3 H3 F2 0.93 2.59 3.381(6) 143.1 5_666
C8 H8 F4' 0.93 2.62 3.119(14) 114.0 3_455
C14 H14 N2 0.93 2.68 3.219(9) 117.6 6_565
C23 H23B F3' 0.97 2.60 3.24(4) 123.7 .
C24 H24B F3' 0.97 2.56 3.12(4) 116.8 .
C3 H3 F2 0.93 2.59 3.381(6) 143.1 5_666
C8 H8 F4' 0.93 2.62 3.119(14) 114.0 3_455
C14 H14 N2 0.93 2.68 3.219(9) 117.6 6_565
C23 H23B F3' 0.97 2.60 3.24(4) 123.7 .
C24 H24B F3' 0.97 2.56 3.12(4) 116.8 .

_refine_diff_density_max         0.474
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.073

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_pn164
_database_code_depnum_ccdc_archive 'CCDC 1041762'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C48 H30 F16 N6 O8 S2 Zn'
_chemical_formula_weight         1252.27

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn 0.2839 1.4301 '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 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   9.1236(4)
_cell_length_b                   14.0611(7)
_cell_length_c                   19.6345(10)
_cell_angle_alpha                90
_cell_angle_beta                 100.7510(10)
_cell_angle_gamma                90
_cell_volume                     2474.7(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9910
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      25.9

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_F_000             1260
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.703
_shelx_estimated_absorpt_T_min   0.766
_shelx_estimated_absorpt_T_max   0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.693
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51157
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0387
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.112
_diffrn_reflns_theta_max         28.308
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6110
_reflns_number_gt                4381
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2012 (Sheldrick, 2012)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


_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)+(0.0686P)²+4.0353P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6110
_refine_ls_number_parameters     364
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0547
_refine_ls_wR_factor_ref         0.1587
_refine_ls_wR_factor_gt          0.1371
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
C1 C 0.5088(3) -0.21568(19) 0.01812(15) 0.0293(6) Uani 1 1 d . . . . .
C2 C 0.5955(4) -0.2982(2) 0.00854(17) 0.0378(7) Uani 1 1 d . . . . .
H2 H 0.5818 -0.3596 0.0238 0.045 Uiso 1 1 calc R U . . .
C3 C 0.7003(4) -0.2695(2) -0.02678(18) 0.0404(8) Uani 1 1 d . . . . .
H3 H 0.7730 -0.3075 -0.0404 0.048 Uiso 1 1 calc R U . . .
C4 C 0.6792(3) -0.16909(19) -0.03962(15) 0.0293(6) Uani 1 1 d . . . . .
C5 C 0.7716(3) -0.1107(2) -0.07173(15) 0.0296(6) Uani 1 1 d . . . . .
C6 C 0.7615(3) -0.01140(19) -0.07903(15) 0.0283(6) Uani 1 1 d . . . . .
C7 C 0.8439(4) 0.0460(2) -0.11949(17) 0.0360(7) Uani 1 1 d . . . . .
H7 H 0.9162 0.0246 -0.1435 0.043 Uiso 1 1 calc R U . . .
C8 C 0.7969(4) 0.1365(2) -0.11609(17) 0.0368(7) Uani 1 1 d . . . . .
H8 H 0.8300 0.1894 -0.1373 0.044 Uiso 1 1 calc R U . . .
C9 C 0.6849(3) 0.13512(19) -0.07286(14) 0.0282(6) Uani 1 1 d . . . . .
C10 C 0.6060(3) 0.21458(19) -0.05699(14) 0.0288(6) Uani 1 1 d . . . . .
C11 C 0.8923(3) -0.15976(19) -0.10000(14) 0.0291(6) Uani 1 1 d . . . . .
C12 C 0.8610(4) -0.2352(2) -0.14653(16) 0.0348(6) Uani 1 1 d . . . . .
H12 H 0.7625 -0.2530 -0.1629 0.042 Uiso 1 1 calc R U . . .
C13 C 0.9741(4) -0.2831(2) -0.16814(17) 0.0375(7) Uani 1 1 d . . . . .
H13 H 0.9520 -0.3345 -0.1981 0.045 Uiso 1 1 calc R U . . .
C14 C 1.1501(4) -0.1830(2) -0.10389(17) 0.0388(7) Uani 1 1 d . . . . .
H14 H 1.2491 -0.1644 -0.0905 0.047 Uiso 1 1 calc R U . . .
C15 C 1.0404(3) -0.1343(2) -0.07956(16) 0.0358(7) Uani 1 1 d . . . . .
H15 H 1.0657 -0.0838 -0.0491 0.043 Uiso 1 1 calc R U . . .
C16 C 1.2377(4) -0.3104(3) -0.1702(2) 0.0571(10) Uani 1 1 d . . . . .
H16A H 1.3101 -0.3294 -0.1305 0.086 Uiso 1 1 calc R U . . .
H16B H 1.2845 -0.2704 -0.1995 0.086 Uiso 1 1 calc R U . . .
H16C H 1.1975 -0.3657 -0.1956 0.086 Uiso 1 1 calc R U . . .
C17 C 0.6357(3) 0.30748(19) -0.08906(15) 0.0306(6) Uani 1 1 d . . . . .
C18 C 0.5615(4) 0.3312(2) -0.15460(16) 0.0359(7) Uani 1 1 d . . . . .
C19 C 0.5772(4) 0.4181(3) -0.18425(18) 0.0452(8) Uani 1 1 d . . . . .
C20 C 0.6717(4) 0.4840(2) -0.1483(2) 0.0469(9) Uani 1 1 d . . . . .
C21 C 0.7500(4) 0.4627(2) -0.0840(2) 0.0465(8) Uani 1 1 d . . . . .
C22 C 0.7318(4) 0.3753(2) -0.05537(18) 0.0408(7) Uani 1 1 d . . . . .
C23 C 0.2591(5) 0.0759(3) -0.1391(2) 0.0687(12) Uani 1 1 d . . . . .
H23A H 0.2033 0.1041 -0.1074 0.103 Uiso 1 1 calc R U . . .
H23B H 0.1919 0.0559 -0.1802 0.103 Uiso 1 1 calc R U . . .
H23C H 0.3279 0.1218 -0.1511 0.103 Uiso 1 1 calc R U . . .
C24 C 0.6137(7) 0.1181(5) 0.3355(3) 0.0895(17) Uani 1 1 d . . . . .
N1 N 0.5606(3) -0.13875(16) -0.01222(12) 0.0281(5) Uani 1 1 d . . . . .
N2 N 0.6660(3) 0.04441(16) -0.05138(12) 0.0278(5) Uani 1 1 d . . . . .
N3 N 1.1159(3) -0.25723(18) -0.14685(14) 0.0364(6) Uani 1 1 d . . . . .
O1 O 0.3386(3) -0.00339(18) -0.10748(13) 0.0501(6) Uani 1 1 d . . . . .
H1 H 0.3820 -0.0295 -0.1354 0.075 Uiso 1 1 calc R U . . .
O2 O 0.3587(5) 0.1348(5) 0.2621(2) 0.138(2) Uani 1 1 d . . . . .
O3 O 0.5628(5) 0.1235(3) 0.20334(18) 0.0929(12) Uani 1 1 d . . . . .
O4 O 0.4874(6) -0.0119(3) 0.2580(3) 0.143(2) Uani 1 1 d . . . . .
F1 F 0.4683(3) 0.26787(15) -0.19059(11) 0.0561(6) Uani 1 1 d . . . . .
F2 F 0.5018(3) 0.43743(19) -0.24776(12) 0.0738(8) Uani 1 1 d . . . . .
F3 F 0.6867(3) 0.56881(15) -0.17698(15) 0.0769(8) Uani 1 1 d . . . . .
F4 F 0.8455(3) 0.52606(16) -0.04969(16) 0.0779(8) Uani 1 1 d . . . . .
F5 F 0.8097(3) 0.35710(16) 0.00825(12) 0.0689(7) Uani 1 1 d . . . . .
F6 F 0.6449(7) 0.2101(4) 0.3389(3) 0.168(2) Uani 1 1 d . . . . .
F7 F 0.7451(4) 0.0775(4) 0.3394(2) 0.1416(17) Uani 1 1 d . . . . .
F8 F 0.5632(5) 0.0969(5) 0.38857(19) 0.197(3) Uani 1 1 d . . . . .
S1 S 0.49107(13) 0.08772(9) 0.25575(6) 0.0627(3) Uiso 1 1 d . . . . .
Zn1 Zn 0.5000 0.0000 0.0000 0.03044(15) Uani 1 2 d S . P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.361(3) . ?
C1 C10 1.407(4) 3_655 ?
C1 C2 1.437(4) . ?
C2 C3 1.343(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.441(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.364(4) . ?
C4 C5 1.408(4) . ?
C5 C6 1.405(4) . ?
C5 C11 1.491(4) . ?
C6 N2 1.359(4) . ?
C6 C7 1.439(4) . ?
C7 C8 1.349(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.445(4) . ?
C8 H8 0.9300 . ?
C9 N2 1.364(3) . ?
C9 C10 1.395(4) . ?
C10 C1 1.407(4) 3_655 ?
C10 C17 1.497(4) . ?
C11 C15 1.383(4) . ?
C11 C12 1.395(4) . ?
C12 C13 1.364(4) . ?
C12 H12 0.9300 . ?
C13 N3 1.334(4) . ?
C13 H13 0.9300 . ?
C14 N3 1.342(4) . ?
C14 C15 1.369(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 N3 1.481(4) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C22 1.378(4) . ?
C17 C18 1.378(4) . ?
C18 F1 1.338(4) . ?
C18 C19 1.373(4) . ?
C19 F2 1.335(4) . ?
C19 C20 1.369(5) . ?
C20 F3 1.337(4) . ?
C20 C21 1.362(6) . ?
C21 F4 1.337(4) . ?
C21 C22 1.375(5) . ?
C22 F5 1.342(4) . ?
C23 O1 1.410(5) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 F8 1.252(6) . ?
C24 F7 1.317(7) . ?
C24 F6 1.323(8) . ?
C24 S1 1.797(6) . ?
N1 Zn1 2.054(2) . ?
N2 Zn1 2.067(2) . ?
O1 Zn1 2.338(3) . ?
O1 H1 0.8200 . ?
O2 S1 1.403(4) . ?
O3 S1 1.411(3) . ?
O4 S1 1.402(4) . ?
Zn1 N1 2.054(2) 3_655 ?
Zn1 N2 2.067(2) 3_655 ?
Zn1 O1 2.338(3) 3_655 ?

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
N1 C1 C10 125.7(3) . 3_655 ?
N1 C1 C2 109.9(2) . . ?
C10 C1 C2 124.3(3) 3_655 . ?
C3 C2 C1 106.7(3) . . ?
C3 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
C2 C3 C4 107.5(3) . . ?
C2 C3 H3 126.3 . . ?
C4 C3 H3 126.3 . . ?
N1 C4 C5 125.4(2) . . ?
N1 C4 C3 109.1(2) . . ?
C5 C4 C3 125.4(3) . . ?
C6 C5 C4 126.3(3) . . ?
C6 C5 C11 117.5(3) . . ?
C4 C5 C11 116.2(2) . . ?
N2 C6 C5 124.6(3) . . ?
N2 C6 C7 109.7(2) . . ?
C5 C6 C7 125.6(3) . . ?
C8 C7 C6 107.3(3) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 106.4(3) . . ?
C7 C8 H8 126.8 . . ?
C9 C8 H8 126.8 . . ?
N2 C9 C10 125.4(2) . . ?
N2 C9 C8 109.8(2) . . ?
C10 C9 C8 124.8(3) . . ?
C9 C10 C1 126.7(3) . 3_655 ?
C9 C10 C17 117.6(2) . . ?
C1 C10 C17 115.5(2) 3_655 . ?
C15 C11 C12 117.1(3) . . ?
C15 C11 C5 121.4(3) . . ?
C12 C11 C5 121.4(3) . . ?
C13 C12 C11 120.3(3) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
N3 C13 C12 120.9(3) . . ?
N3 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
N3 C14 C15 120.6(3) . . ?
N3 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C14 C15 C11 120.5(3) . . ?
C14 C15 H15 119.7 . . ?
C11 C15 H15 119.7 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C22 C17 C18 116.0(3) . . ?
C22 C17 C10 123.4(3) . . ?
C18 C17 C10 120.5(3) . . ?
F1 C18 C19 118.3(3) . . ?
F1 C18 C17 119.0(3) . . ?
C19 C18 C17 122.6(3) . . ?
F2 C19 C20 120.6(3) . . ?
F2 C19 C18 120.1(3) . . ?
C20 C19 C18 119.3(3) . . ?
F3 C20 C21 120.6(3) . . ?
F3 C20 C19 119.3(4) . . ?
C21 C20 C19 120.1(3) . . ?
F4 C21 C20 120.0(3) . . ?
F4 C21 C22 120.5(3) . . ?
C20 C21 C22 119.5(3) . . ?
F5 C22 C21 117.9(3) . . ?
F5 C22 C17 119.6(3) . . ?
C21 C22 C17 122.5(3) . . ?
O1 C23 H23A 109.5 . . ?
O1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
F8 C24 F7 108.7(6) . . ?
F8 C24 F6 107.4(7) . . ?
F7 C24 F6 103.6(5) . . ?
F8 C24 S1 113.7(4) . . ?
F7 C24 S1 111.1(5) . . ?
F6 C24 S1 111.7(5) . . ?
C1 N1 C4 106.9(2) . . ?
C1 N1 Zn1 125.49(19) . . ?
C4 N1 Zn1 126.43(18) . . ?
C6 N2 C9 106.8(2) . . ?
C6 N2 Zn1 127.11(18) . . ?
C9 N2 Zn1 125.45(18) . . ?
C13 N3 C14 120.5(3) . . ?
C13 N3 C16 120.4(3) . . ?
C14 N3 C16 119.2(3) . . ?
C23 O1 Zn1 124.5(2) . . ?
C23 O1 H1 109.5 . . ?
Zn1 O1 H1 108.1 . . ?
O4 S1 O2 116.3(4) . . ?
O4 S1 O3 113.3(3) . . ?
O2 S1 O3 114.9(3) . . ?
O4 S1 C24 103.0(3) . . ?
O2 S1 C24 102.5(3) . . ?
O3 S1 C24 104.6(3) . . ?
N1 Zn1 N1 180.00(13) 3_655 . ?
N1 Zn1 N2 89.56(9) 3_655 3_655 ?
N1 Zn1 N2 90.44(9) . 3_655 ?
N1 Zn1 N2 90.44(9) 3_655 . ?
N1 Zn1 N2 89.56(9) . . ?
N2 Zn1 N2 180.00(7) 3_655 . ?
N1 Zn1 O1 90.75(9) 3_655 3_655 ?
N1 Zn1 O1 89.25(9) . 3_655 ?
N2 Zn1 O1 87.76(9) 3_655 3_655 ?
N2 Zn1 O1 92.24(9) . 3_655 ?
N1 Zn1 O1 89.25(9) 3_655 . ?
N1 Zn1 O1 90.75(9) . . ?
N2 Zn1 O1 92.24(9) 3_655 . ?
N2 Zn1 O1 87.76(9) . . ?
O1 Zn1 O1 180.0 3_655 . ?

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
N1 C1 C2 C3 0.8(4) . . . . ?
C10 C1 C2 C3 -175.5(3) 3_655 . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 N1 -0.5(4) . . . . ?
C2 C3 C4 C5 176.1(3) . . . . ?
N1 C4 C5 C6 2.4(5) . . . . ?
C3 C4 C5 C6 -173.7(3) . . . . ?
N1 C4 C5 C11 -178.2(3) . . . . ?
C3 C4 C5 C11 5.8(4) . . . . ?
C4 C5 C6 N2 5.0(5) . . . . ?
C11 C5 C6 N2 -174.5(3) . . . . ?
C4 C5 C6 C7 -171.6(3) . . . . ?
C11 C5 C6 C7 8.9(4) . . . . ?
N2 C6 C7 C8 -0.2(4) . . . . ?
C5 C6 C7 C8 176.8(3) . . . . ?
C6 C7 C8 C9 0.3(4) . . . . ?
C7 C8 C9 N2 -0.3(4) . . . . ?
C7 C8 C9 C10 -178.9(3) . . . . ?
N2 C9 C10 C1 -1.9(5) . . . 3_655 ?
C8 C9 C10 C1 176.6(3) . . . 3_655 ?
N2 C9 C10 C17 -176.2(3) . . . . ?
C8 C9 C10 C17 2.2(4) . . . . ?
C6 C5 C11 C15 55.8(4) . . . . ?
C4 C5 C11 C15 -123.7(3) . . . . ?
C6 C5 C11 C12 -126.2(3) . . . . ?
C4 C5 C11 C12 54.2(4) . . . . ?
C15 C11 C12 C13 2.4(4) . . . . ?
C5 C11 C12 C13 -175.7(3) . . . . ?
C11 C12 C13 N3 -1.8(5) . . . . ?
N3 C14 C15 C11 -1.3(5) . . . . ?
C12 C11 C15 C14 -0.8(5) . . . . ?
C5 C11 C15 C14 177.2(3) . . . . ?
C9 C10 C17 C22 -97.6(4) . . . . ?
C1 C10 C17 C22 87.4(4) 3_655 . . . ?
C9 C10 C17 C18 85.0(4) . . . . ?
C1 C10 C17 C18 -90.0(3) 3_655 . . . ?
C22 C17 C18 F1 179.0(3) . . . . ?
C10 C17 C18 F1 -3.4(4) . . . . ?
C22 C17 C18 C19 -2.2(5) . . . . ?
C10 C17 C18 C19 175.4(3) . . . . ?
F1 C18 C19 F2 -0.8(5) . . . . ?
C17 C18 C19 F2 -179.6(3) . . . . ?
F1 C18 C19 C20 179.9(3) . . . . ?
C17 C18 C19 C20 1.0(5) . . . . ?
F2 C19 C20 F3 0.8(6) . . . . ?
C18 C19 C20 F3 -179.8(3) . . . . ?
F2 C19 C20 C21 -178.8(3) . . . . ?
C18 C19 C20 C21 0.6(6) . . . . ?
F3 C20 C21 F4 -1.6(6) . . . . ?
C19 C20 C21 F4 178.1(3) . . . . ?
F3 C20 C21 C22 179.5(3) . . . . ?
C19 C20 C21 C22 -0.9(6) . . . . ?
F4 C21 C22 F5 1.6(5) . . . . ?
C20 C21 C22 F5 -179.4(3) . . . . ?
F4 C21 C22 C17 -179.4(3) . . . . ?
C20 C21 C22 C17 -0.5(6) . . . . ?
C18 C17 C22 F5 -179.1(3) . . . . ?
C10 C17 C22 F5 3.4(5) . . . . ?
C18 C17 C22 C21 1.9(5) . . . . ?
C10 C17 C22 C21 -175.6(3) . . . . ?
C10 C1 N1 C4 175.1(3) 3_655 . . . ?
C2 C1 N1 C4 -1.2(3) . . . . ?
C10 C1 N1 Zn1 7.1(4) 3_655 . . . ?
C2 C1 N1 Zn1 -169.2(2) . . . . ?
C5 C4 N1 C1 -175.6(3) . . . . ?
C3 C4 N1 C1 1.0(3) . . . . ?
C5 C4 N1 Zn1 -7.7(4) . . . . ?
C3 C4 N1 Zn1 168.9(2) . . . . ?
C5 C6 N2 C9 -177.0(3) . . . . ?
C7 C6 N2 C9 0.0(3) . . . . ?
C5 C6 N2 Zn1 -6.0(4) . . . . ?
C7 C6 N2 Zn1 171.1(2) . . . . ?
C10 C9 N2 C6 178.8(3) . . . . ?
C8 C9 N2 C6 0.2(3) . . . . ?
C10 C9 N2 Zn1 7.6(4) . . . . ?
C8 C9 N2 Zn1 -171.1(2) . . . . ?
C12 C13 N3 C14 -0.4(5) . . . . ?
C12 C13 N3 C16 179.4(3) . . . . ?
C15 C14 N3 C13 2.0(5) . . . . ?
C15 C14 N3 C16 -177.8(3) . . . . ?
F8 C24 S1 O4 -65.5(7) . . . . ?
F7 C24 S1 O4 57.5(6) . . . . ?
F6 C24 S1 O4 172.7(5) . . . . ?
F8 C24 S1 O2 55.5(7) . . . . ?
F7 C24 S1 O2 178.6(5) . . . . ?
F6 C24 S1 O2 -66.3(5) . . . . ?
F8 C24 S1 O3 175.8(6) . . . . ?
F7 C24 S1 O3 -61.2(5) . . . . ?
F6 C24 S1 O3 54.0(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
C3 H3 F4 0.93 2.45 3.232(4) 142.0 1_545
C12 H12 F3 0.93 2.60 3.182(4) 121.1 1_545
C13 H13 O4 0.93 2.37 3.240(5) 155.5 4_655
C14 H14 O1 0.93 2.45 3.063(4) 123.5 1_655
C16 H16B O3 0.96 2.50 3.329(6) 144.6 3_755
C16 H16C O4 0.96 2.61 3.500(7) 154.3 4_655
C23 H23C F1 0.96 2.61 3.560(5) 168.6 .
O1 H1 O3 0.82 2.01 2.799(5) 161.9 3_655
O1 H1 S1 0.82 2.94 3.739(3) 167.1 3_655

_refine_diff_density_max         1.023
_refine_diff_density_min         -1.517
_refine_diff_density_rms         0.077

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_PN152
_database_code_depnum_ccdc_archive 'CCDC 1058021'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-06-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H24 F16 N6 O8 S2'
_chemical_formula_weight         1156.83

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'
S S 0.1246 0.1234 '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 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   13.5879(17)
_cell_length_b                   11.0738(10)
_cell_length_c                   17.130(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.223(4)
_cell_angle_gamma                90
_cell_volume                     2368.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5528
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      23.01

_exptl_crystal_description       block
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.622
_exptl_crystal_F_000             1164
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.237
_shelx_estimated_absorpt_T_min   0.932
_shelx_estimated_absorpt_T_max   0.943
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_T_max  0.932
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33767
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.249
_diffrn_reflns_theta_max         24.995
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4175
_reflns_number_gt                2623
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0573P)²+4.6134P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4175
_refine_ls_number_parameters     495
_refine_ls_number_restraints     499
_refine_ls_R_factor_all          0.1302
_refine_ls_R_factor_gt           0.0779
_refine_ls_wR_factor_ref         0.2002
_refine_ls_wR_factor_gt          0.1632
_refine_ls_goodness_of_fit_ref   1.137
_refine_ls_restrained_S_all      1.123
_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
C1 C -0.2195(3) -0.1039(4) 0.9752(3) 0.0417(11) Uani 1 1 d . . . . .
C2 C -0.3283(4) -0.1114(4) 0.9138(3) 0.0504(12) Uani 1 1 d . . . . .
H2 H -0.3851 -0.1501 0.9208 0.061 Uiso 1 1 calc R U . . .
C3 C -0.3318(4) -0.0518(4) 0.8451(3) 0.0493(12) Uani 1 1 d . . . . .
H3 H -0.3917 -0.0414 0.7948 0.059 Uiso 1 1 calc R U . . .
C4 C -0.2257(3) -0.0067(4) 0.8633(3) 0.0407(10) Uani 1 1 d . . . . .
C5 C -0.1973(3) 0.0611(4) 0.8068(3) 0.0408(11) Uani 1 1 d . . . . .
C6 C -0.0953(4) 0.1037(4) 0.8209(3) 0.0417(10) Uani 1 1 d . . . . .
C7 C -0.0662(4) 0.1732(4) 0.7631(3) 0.0557(13) Uani 1 1 d . . . . .
H7 H -0.1122 0.1969 0.7089 0.067 Uiso 1 1 calc R U . . .
C8 C 0.0381(4) 0.1984(4) 0.8002(3) 0.0544(13) Uani 1 1 d . . . . .
H8 H 0.0774 0.2422 0.7762 0.065 Uiso 1 1 calc R U . . .
C9 C 0.0784(3) 0.1470(4) 0.8822(3) 0.0419(11) Uani 1 1 d . . . . .
C10 C 0.1825(3) 0.1532(4) 0.9437(3) 0.0410(11) Uani 1 1 d D . . . .
C11 C 0.2599(10) 0.2179(7) 0.9160(10) 0.039(3) Uani 0.681(14) 1 d D U P A 1
C12 C 0.2510(8) 0.3404(6) 0.9017(7) 0.051(2) Uani 0.681(14) 1 d D U P A 1
H12 H 0.1964 0.3832 0.9092 0.061 Uiso 0.681(14) 1 calc R U P A 1
C13 C 0.3216(8) 0.3994(8) 0.8767(7) 0.056(2) Uani 0.681(14) 1 d D U P A 1
H13 H 0.3152 0.4821 0.8668 0.067 Uiso 0.681(14) 1 calc R U P A 1
N3 N 0.3991(12) 0.3383(10) 0.8667(11) 0.055(3) Uani 0.681(14) 1 d D U P A 1
C14 C 0.4109(8) 0.2207(10) 0.8795(7) 0.051(3) Uani 0.681(14) 1 d D U P A 1
H14 H 0.4663 0.1804 0.8716 0.062 Uiso 0.681(14) 1 calc R U P A 1
C15 C 0.3416(7) 0.1580(9) 0.9045(6) 0.041(2) Uani 0.681(14) 1 d D U P A 1
H15 H 0.3498 0.0752 0.9137 0.049 Uiso 0.681(14) 1 calc R U P A 1
C16 C 0.4647(15) 0.408(2) 0.8299(11) 0.088(6) Uani 0.681(14) 1 d D U P A 1
H16A H 0.4263 0.4147 0.7696 0.132 Uiso 0.681(14) 1 calc R U P A 1
H16B H 0.5313 0.3670 0.8420 0.132 Uiso 0.681(14) 1 calc R U P A 1
H16C H 0.4786 0.4873 0.8546 0.132 Uiso 0.681(14) 1 calc R U P A 1
C11' C 0.263(2) 0.2242(17) 0.923(2) 0.046(6) Uani 0.319(14) 1 d D U P A 2
C12' C 0.2914(16) 0.3412(15) 0.9490(15) 0.057(4) Uani 0.319(14) 1 d D U P A 2
H12' H 0.2637 0.3798 0.9841 0.068 Uiso 0.319(14) 1 calc R U P A 2
C13' C 0.3610(17) 0.4003(19) 0.9221(16) 0.059(4) Uani 0.319(14) 1 d D U P A 2
H13' H 0.3792 0.4795 0.9401 0.070 Uiso 0.319(14) 1 calc R U P A 2
N3' N 0.404(3) 0.352(2) 0.872(2) 0.058(5) Uani 0.319(14) 1 d D U P A 2
C14' C 0.380(2) 0.238(2) 0.8515(16) 0.059(5) Uani 0.319(14) 1 d D U P A 2
H14' H 0.4130 0.1997 0.8194 0.071 Uiso 0.319(14) 1 calc R U P A 2
C15' C 0.3108(18) 0.172(2) 0.8745(14) 0.054(5) Uani 0.319(14) 1 d D U P A 2
H15' H 0.2959 0.0920 0.8571 0.065 Uiso 0.319(14) 1 calc R U P A 2
C16' C 0.494(2) 0.414(4) 0.859(2) 0.052(6) Uani 0.319(14) 1 d D U P A 2
H16D H 0.4676 0.4857 0.8264 0.078 Uiso 0.319(14) 1 calc R U P A 2
H16E H 0.5228 0.3605 0.8294 0.078 Uiso 0.319(14) 1 calc R U P A 2
H16F H 0.5485 0.4343 0.9132 0.078 Uiso 0.319(14) 1 calc R U P A 2
C17 C -0.2844(3) 0.0975(4) 0.7257(3) 0.0455(11) Uani 1 1 d . . . . .
C18 C -0.3567(4) 0.1858(5) 0.7249(4) 0.0595(14) Uani 1 1 d . . . . .
C19 C -0.4355(5) 0.2250(5) 0.6532(5) 0.0761(18) Uani 1 1 d . . . . .
C20 C -0.4472(5) 0.1769(6) 0.5771(4) 0.078(2) Uani 1 1 d . . . . .
C21 C -0.3782(5) 0.0882(6) 0.5746(3) 0.0715(17) Uani 1 1 d . . . . .
C22 C -0.2977(4) 0.0505(5) 0.6478(3) 0.0551(13) Uani 1 1 d . . . . .
N1 N -0.1581(3) -0.0407(3) 0.9426(2) 0.0414(9) Uani 1 1 d . . . . .
N2 N -0.0054(3) 0.0885(3) 0.8920(2) 0.0392(9) Uani 1 1 d D . . . .
F1 F -0.3488(3) 0.2341(3) 0.7989(2) 0.0951(12) Uani 1 1 d . . . . .
F2 F -0.5026(3) 0.3113(4) 0.6563(3) 0.1298(17) Uani 1 1 d . . . . .
F3 F -0.5254(3) 0.2125(4) 0.5056(3) 0.1279(18) Uani 1 1 d . . . . .
F4 F -0.3893(3) 0.0394(4) 0.5004(2) 0.1112(14) Uani 1 1 d . . . . .
F5 F -0.2306(3) -0.0348(3) 0.6434(2) 0.0864(11) Uani 1 1 d . . . . .
H2A H 0.002(5) 0.051(5) 0.937(2) 0.09(2) Uiso 1 1 d D . . . .
C23 C 0.2138(15) 0.2899(14) 0.5574(12) 0.118(6) Uani 0.625(18) 1 d D U P B 3
F6 F 0.2594(13) 0.1949(10) 0.5427(11) 0.163(5) Uani 0.625(18) 1 d D U P B 3
F7 F 0.1512(13) 0.3419(14) 0.4844(7) 0.164(5) Uani 0.625(18) 1 d D U P B 3
F8 F 0.2878(12) 0.3710(14) 0.5992(11) 0.137(5) Uani 0.625(18) 1 d D U P B 3
S1 S 0.1370(7) 0.2572(7) 0.6189(5) 0.094(3) Uani 0.625(18) 1 d D U P B 3
O1 O 0.0572(11) 0.1782(12) 0.5654(10) 0.106(5) Uani 0.625(18) 1 d D U P B 3
O2 O 0.1025(10) 0.3668(8) 0.6388(10) 0.110(4) Uani 0.625(18) 1 d D U P B 3
O3 O 0.2151(10) 0.1955(13) 0.6899(7) 0.098(3) Uani 0.625(18) 1 d D U P B 3
C23' C 0.187(2) 0.298(2) 0.5435(14) 0.092(7) Uani 0.375(18) 1 d D U P B 4
F6' F 0.184(2) 0.2013(18) 0.4992(14) 0.158(6) Uani 0.375(18) 1 d D U P B 4
F7' F 0.111(2) 0.376(2) 0.503(2) 0.205(10) Uani 0.375(18) 1 d D U P B 4
F8' F 0.280(2) 0.351(3) 0.567(2) 0.149(8) Uani 0.375(18) 1 d D U P B 4
S1' S 0.1489(9) 0.2566(6) 0.6266(5) 0.051(2) Uani 0.375(18) 1 d D U P B 4
O2' O 0.159(2) 0.3621(15) 0.6736(14) 0.128(7) Uani 0.375(18) 1 d D U P B 4
O1' O 0.0483(15) 0.202(2) 0.590(2) 0.114(7) Uani 0.375(18) 1 d D U P B 4
O3' O 0.2326(19) 0.171(2) 0.6699(19) 0.152(10) Uani 0.375(18) 1 d D U P B 4
O4 O 0.0889(5) 0.5359(6) 0.7683(4) 0.153(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
C1 N1 1.367(5) . ?
C1 C10 1.389(6) 3_557 ?
C1 C2 1.440(6) . ?
C2 C3 1.334(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.439(6) . ?
C3 H3 0.9300 . ?
C4 N1 1.358(5) . ?
C4 C5 1.395(6) . ?
C5 C6 1.391(6) . ?
C5 C17 1.483(6) . ?
C6 N2 1.353(6) . ?
C6 C7 1.427(6) . ?
C7 C8 1.334(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.411(6) . ?
C8 H8 0.9300 . ?
C9 N2 1.375(5) . ?
C9 C10 1.393(6) . ?
C10 C1 1.389(6) 3_557 ?
C10 C11 1.495(7) . ?
C10 C11' 1.496(10) . ?
C11 C15 1.372(7) . ?
C11 C12 1.376(7) . ?
C12 C13 1.362(6) . ?
C12 H12 0.9300 . ?
C13 N3 1.319(7) . ?
C13 H13 0.9300 . ?
N3 C14 1.320(7) . ?
N3 C16 1.493(10) . ?
C14 C15 1.366(6) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C11' C15' 1.372(8) . ?
C11' C12' 1.373(8) . ?
C12' C13' 1.371(8) . ?
C12' H12' 0.9300 . ?
C13' N3' 1.320(9) . ?
C13' H13' 0.9300 . ?
N3' C14' 1.320(9) . ?
N3' C16' 1.493(11) . ?
C14' C15' 1.370(8) . ?
C14' H14' 0.9300 . ?
C15' H15' 0.9300 . ?
C16' H16D 0.9600 . ?
C16' H16E 0.9600 . ?
C16' H16F 0.9600 . ?
C17 C22 1.376(7) . ?
C17 C18 1.382(7) . ?
C18 F1 1.341(6) . ?
C18 C19 1.344(8) . ?
C19 F2 1.336(7) . ?
C19 C20 1.358(9) . ?
C20 F3 1.326(6) . ?
C20 C21 1.371(9) . ?
C21 F4 1.333(7) . ?
C21 C22 1.365(7) . ?
C22 F5 1.335(6) . ?
N2 H2A 0.85(2) . ?
C23 F6 1.295(13) . ?
C23 F8 1.327(12) . ?
C23 F7 1.335(13) . ?
C23 S1 1.79(2) . ?
S1 O2 1.391(8) . ?
S1 O1 1.413(9) . ?
S1 O3 1.433(9) . ?
C23' F6' 1.298(14) . ?
C23' F8' 1.309(14) . ?
C23' F7' 1.320(15) . ?
C23' S1' 1.76(2) . ?
S1' O2' 1.395(12) . ?
S1' O1' 1.396(13) . ?
S1' O3' 1.442(12) . ?

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
N1 C1 C10 124.9(4) . 3_557 ?
N1 C1 C2 110.3(4) . . ?
C10 C1 C2 124.7(4) 3_557 . ?
C3 C2 C1 106.6(4) . . ?
C3 C2 H2 126.7 . . ?
C1 C2 H2 126.7 . . ?
C2 C3 C4 107.3(4) . . ?
C2 C3 H3 126.4 . . ?
C4 C3 H3 126.4 . . ?
N1 C4 C5 125.4(4) . . ?
N1 C4 C3 110.2(4) . . ?
C5 C4 C3 124.4(4) . . ?
C6 C5 C4 126.3(4) . . ?
C6 C5 C17 116.3(4) . . ?
C4 C5 C17 117.3(4) . . ?
N2 C6 C5 126.7(4) . . ?
N2 C6 C7 107.0(4) . . ?
C5 C6 C7 126.3(4) . . ?
C8 C7 C6 108.4(4) . . ?
C8 C7 H7 125.8 . . ?
C6 C7 H7 125.8 . . ?
C7 C8 C9 108.2(4) . . ?
C7 C8 H8 125.9 . . ?
C9 C8 H8 125.9 . . ?
N2 C9 C10 125.0(4) . . ?
N2 C9 C8 107.2(4) . . ?
C10 C9 C8 127.7(4) . . ?
C1 C10 C9 126.5(4) 3_557 . ?
C1 C10 C11 118.9(8) 3_557 . ?
C9 C10 C11 114.6(7) . . ?
C1 C10 C11' 115.5(16) 3_557 . ?
C9 C10 C11' 117.9(16) . . ?
C15 C11 C12 118.1(6) . . ?
C15 C11 C10 121.6(7) . . ?
C12 C11 C10 120.3(7) . . ?
C13 C12 C11 120.3(7) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
N3 C13 C12 119.6(9) . . ?
N3 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 N3 C14 122.3(11) . . ?
C13 N3 C16 115.4(13) . . ?
C14 N3 C16 121.9(13) . . ?
N3 C14 C15 120.0(10) . . ?
N3 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C11 119.7(8) . . ?
C14 C15 H15 120.1 . . ?
C11 C15 H15 120.1 . . ?
N3 C16 H16A 109.5 . . ?
N3 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N3 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15' C11' C12' 117.0(14) . . ?
C15' C11' C10 119.0(15) . . ?
C12' C11' C10 124.0(14) . . ?
C13' C12' C11' 119.1(16) . . ?
C13' C12' H12' 120.5 . . ?
C11' C12' H12' 120.5 . . ?
N3' C13' C12' 124(2) . . ?
N3' C13' H13' 117.9 . . ?
C12' C13' H13' 117.9 . . ?
C14' N3' C13' 116(3) . . ?
C14' N3' C16' 121(2) . . ?
C13' N3' C16' 120(2) . . ?
N3' C14' C15' 123(3) . . ?
N3' C14' H14' 118.3 . . ?
C15' C14' H14' 118.3 . . ?
C14' C15' C11' 120(2) . . ?
C14' C15' H15' 120.1 . . ?
C11' C15' H15' 120.1 . . ?
N3' C16' H16D 109.5 . . ?
N3' C16' H16E 109.5 . . ?
H16D C16' H16E 109.5 . . ?
N3' C16' H16F 109.5 . . ?
H16D C16' H16F 109.5 . . ?
H16E C16' H16F 109.5 . . ?
C22 C17 C18 115.9(4) . . ?
C22 C17 C5 123.8(4) . . ?
C18 C17 C5 120.2(4) . . ?
F1 C18 C19 118.2(5) . . ?
F1 C18 C17 118.8(5) . . ?
C19 C18 C17 123.0(6) . . ?
F2 C19 C18 120.3(7) . . ?
F2 C19 C20 119.7(6) . . ?
C18 C19 C20 119.9(6) . . ?
F3 C20 C19 121.2(7) . . ?
F3 C20 C21 119.5(7) . . ?
C19 C20 C21 119.3(5) . . ?
F4 C21 C22 120.0(6) . . ?
F4 C21 C20 120.0(6) . . ?
C22 C21 C20 120.0(6) . . ?
F5 C22 C21 118.8(5) . . ?
F5 C22 C17 119.5(4) . . ?
C21 C22 C17 121.7(5) . . ?
C4 N1 C1 105.6(4) . . ?
C6 N2 C9 109.2(4) . . ?
C6 N2 H2A 129(4) . . ?
C9 N2 H2A 122(4) . . ?
F6 C23 F8 109.7(13) . . ?
F6 C23 F7 110.2(15) . . ?
F8 C23 F7 106.3(12) . . ?
F6 C23 S1 112.7(13) . . ?
F8 C23 S1 108.2(13) . . ?
F7 C23 S1 109.6(13) . . ?
O2 S1 O1 116.9(8) . . ?
O2 S1 O3 114.6(8) . . ?
O1 S1 O3 112.2(7) . . ?
O2 S1 C23 107.4(8) . . ?
O1 S1 C23 102.7(10) . . ?
O3 S1 C23 100.8(9) . . ?
F6' C23' F8' 111.3(14) . . ?
F6' C23' F7' 112.8(15) . . ?
F8' C23' F7' 109.0(15) . . ?
F6' C23' S1' 107.9(16) . . ?
F8' C23' S1' 115(2) . . ?
F7' C23' S1' 100.2(19) . . ?
O2' S1' O1' 118.5(12) . . ?
O2' S1' O3' 112.1(10) . . ?
O1' S1' O3' 112.5(11) . . ?
O2' S1' C23' 104.9(13) . . ?
O1' S1' C23' 107.3(17) . . ?
O3' S1' C23' 99.2(17) . . ?

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
N1 C1 C2 C3 -0.5(5) . . . . ?
C10 C1 C2 C3 179.0(4) 3_557 . . . ?
C1 C2 C3 C4 -0.2(5) . . . . ?
C2 C3 C4 N1 0.9(5) . . . . ?
C2 C3 C4 C5 -179.6(4) . . . . ?
N1 C4 C5 C6 1.2(7) . . . . ?
C3 C4 C5 C6 -178.1(4) . . . . ?
N1 C4 C5 C17 -175.2(4) . . . . ?
C3 C4 C5 C17 5.4(6) . . . . ?
C4 C5 C6 N2 -0.8(7) . . . . ?
C17 C5 C6 N2 175.6(4) . . . . ?
C4 C5 C6 C7 -179.9(4) . . . . ?
C17 C5 C6 C7 -3.5(7) . . . . ?
N2 C6 C7 C8 -0.4(6) . . . . ?
C5 C6 C7 C8 178.9(5) . . . . ?
C6 C7 C8 C9 -0.4(6) . . . . ?
C7 C8 C9 N2 1.0(6) . . . . ?
C7 C8 C9 C10 -178.5(5) . . . . ?
N2 C9 C10 C1 -1.0(7) . . . 3_557 ?
C8 C9 C10 C1 178.5(5) . . . 3_557 ?
N2 C9 C10 C11 177.6(5) . . . . ?
C8 C9 C10 C11 -3.0(7) . . . . ?
N2 C9 C10 C11' -178.1(9) . . . . ?
C8 C9 C10 C11' 1.4(11) . . . . ?
C1 C10 C11 C15 66.8(15) 3_557 . . . ?
C9 C10 C11 C15 -111.9(13) . . . . ?
C11' C10 C11 C15 116(21) . . . . ?
C1 C10 C11 C12 -112.8(13) 3_557 . . . ?
C9 C10 C11 C12 68.5(14) . . . . ?
C11' C10 C11 C12 -63(19) . . . . ?
C15 C11 C12 C13 0.2(19) . . . . ?
C10 C11 C12 C13 179.8(10) . . . . ?
C11 C12 C13 N3 -0.4(18) . . . . ?
C12 C13 N3 C14 0(2) . . . . ?
C12 C13 N3 C16 173.4(12) . . . . ?
C13 N3 C14 C15 0(2) . . . . ?
C16 N3 C14 C15 -172.8(13) . . . . ?
N3 C14 C15 C11 0.1(17) . . . . ?
C12 C11 C15 C14 -0.1(18) . . . . ?
C10 C11 C15 C14 -179.7(10) . . . . ?
C1 C10 C11' C15' 102(3) 3_557 . . . ?
C9 C10 C11' C15' -81(3) . . . . ?
C11 C10 C11' C15' -30(17) . . . . ?
C1 C10 C11' C12' -80(3) 3_557 . . . ?
C9 C10 C11' C12' 98(3) . . . . ?
C11 C10 C11' C12' 148(23) . . . . ?
C15' C11' C12' C13' 3(4) . . . . ?
C10 C11' C12' C13' -176(2) . . . . ?
C11' C12' C13' N3' 0(4) . . . . ?
C12' C13' N3' C14' -3(5) . . . . ?
C12' C13' N3' C16' -169(3) . . . . ?
C13' N3' C14' C15' 4(5) . . . . ?
C16' N3' C14' C15' 169(3) . . . . ?
N3' C14' C15' C11' -1(4) . . . . ?
C12' C11' C15' C14' -2(4) . . . . ?
C10 C11' C15' C14' 177(2) . . . . ?
C6 C5 C17 C22 73.7(6) . . . . ?
C4 C5 C17 C22 -109.6(5) . . . . ?
C6 C5 C17 C18 -104.5(5) . . . . ?
C4 C5 C17 C18 72.3(6) . . . . ?
C22 C17 C18 F1 179.2(4) . . . . ?
C5 C17 C18 F1 -2.5(7) . . . . ?
C22 C17 C18 C19 -0.2(7) . . . . ?
C5 C17 C18 C19 178.1(5) . . . . ?
F1 C18 C19 F2 1.1(8) . . . . ?
C17 C18 C19 F2 -179.5(5) . . . . ?
F1 C18 C19 C20 -178.9(5) . . . . ?
C17 C18 C19 C20 0.5(9) . . . . ?
F2 C19 C20 F3 -1.2(9) . . . . ?
C18 C19 C20 F3 178.8(5) . . . . ?
F2 C19 C20 C21 -179.8(5) . . . . ?
C18 C19 C20 C21 0.2(9) . . . . ?
F3 C20 C21 F4 0.8(8) . . . . ?
C19 C20 C21 F4 179.4(5) . . . . ?
F3 C20 C21 C22 -179.7(5) . . . . ?
C19 C20 C21 C22 -1.1(8) . . . . ?
F4 C21 C22 F5 0.5(7) . . . . ?
C20 C21 C22 F5 -179.0(5) . . . . ?
F4 C21 C22 C17 -179.2(4) . . . . ?
C20 C21 C22 C17 1.4(8) . . . . ?
C18 C17 C22 F5 179.7(4) . . . . ?
C5 C17 C22 F5 1.4(7) . . . . ?
C18 C17 C22 C21 -0.7(7) . . . . ?
C5 C17 C22 C21 -178.9(5) . . . . ?
C5 C4 N1 C1 179.4(4) . . . . ?
C3 C4 N1 C1 -1.2(5) . . . . ?
C10 C1 N1 C4 -178.5(4) 3_557 . . . ?
C2 C1 N1 C4 1.1(5) . . . . ?
C5 C6 N2 C9 -178.2(4) . . . . ?
C7 C6 N2 C9 1.1(5) . . . . ?
C10 C9 N2 C6 178.3(4) . . . . ?
C8 C9 N2 C6 -1.3(5) . . . . ?
F6 C23 S1 O2 173.3(11) . . . . ?
F8 C23 S1 O2 51.8(12) . . . . ?
F7 C23 S1 O2 -63.6(12) . . . . ?
F6 C23 S1 O1 -62.9(13) . . . . ?
F8 C23 S1 O1 175.7(11) . . . . ?
F7 C23 S1 O1 60.2(12) . . . . ?
F6 C23 S1 O3 53.0(13) . . . . ?
F8 C23 S1 O3 -68.5(12) . . . . ?
F7 C23 S1 O3 176.1(10) . . . . ?
F6' C23' S1' O2' 177.4(15) . . . . ?
F8' C23' S1' O2' 52.4(17) . . . . ?
F7' C23' S1' O2' -64.4(15) . . . . ?
F6' C23' S1' O1' -55.7(19) . . . . ?
F8' C23' S1' O1' 179.3(17) . . . . ?
F7' C23' S1' O1' 62.5(18) . . . . ?
F6' C23' S1' O3' 61.5(18) . . . . ?
F8' C23' S1' O3' -63.5(18) . . . . ?
F7' C23' S1' O3' 179.7(16) . . . . ?

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
C3 H3 O4 0.93 2.61 3.402(8) 143.6 2_446
C12 H12 F4 0.93 2.44 3.286(9) 150.9 4_666
C16 H16B F1 0.96 2.51 3.39(2) 151.6 1_655
C12' H12' F4 0.93 2.38 3.203(19) 147.6 4_666
C14' H14' O4 0.93 2.35 3.17(3) 146.9 2_546
C16' H16E F1 0.96 2.45 3.37(4) 160.2 1_655
N2 H2A N1 0.85(2) 2.44(5) 2.919(5) 117(5) .
N2 H2A N1 0.85(2) 2.30(5) 2.878(5) 125(5) 3_557
C3 H3 O4 0.93 2.61 3.402(8) 143.6 2_446
C12 H12 F4 0.93 2.44 3.286(9) 150.9 4_666
C16 H16B F1 0.96 2.51 3.39(2) 151.6 1_655
C12' H12' F4 0.93 2.38 3.203(19) 147.6 4_666
C14' H14' O4 0.93 2.35 3.17(3) 146.9 2_546
C16' H16E F1 0.96 2.45 3.37(4) 160.2 1_655
N2 H2A N1 0.85(2) 2.44(5) 2.919(5) 117(5) .
N2 H2A N1 0.85(2) 2.30(5) 2.878(5) 125(5) 3_557

_refine_diff_density_max         0.711
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.059

_shelxl_version_number           2012-9

####################################################################### 
# 
# 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_190
_database_code_depnum_ccdc_archive 'CCDC 1434316'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-06-22 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            'C21 H9 F5 N3'
_chemical_formula_weight         398.31

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   15.113(3)
_cell_length_b                   10.4895(16)
_cell_length_c                   11.628(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.085(9)
_cell_angle_gamma                90
_cell_volume                     1708.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3955
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      22.5

_exptl_crystal_description       plate
_exptl_crystal_colour            black
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.132
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.902
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24166
_diffrn_reflns_av_unetI/netI     0.1735
_diffrn_reflns_av_R_equivalents  0.2114
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.426
_diffrn_reflns_theta_max         23.195
_diffrn_reflns_theta_full        23.195
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.978
_reflns_number_total             2397
_reflns_number_gt                1127
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0294P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0057(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2397
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1741
_refine_ls_R_factor_gt           0.0595
_refine_ls_wR_factor_ref         0.0900
_refine_ls_wR_factor_gt          0.0718
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_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
C1 C 0.5118(3) 0.6226(3) 0.2651(3) 0.0343(9) Uani 1 1 d . . . . .
C2 C 0.4543(3) 0.6950(3) 0.1605(3) 0.0467(11) Uani 1 1 d . . . . .
H2 H 0.4743 0.7308 0.1013 0.056 Uiso 1 1 calc R U . . .
C3 C 0.3658(3) 0.7028(3) 0.1618(3) 0.0448(11) Uani 1 1 d . . . . .
H3 H 0.3141 0.7441 0.1031 0.054 Uiso 1 1 calc R U . . .
C4 C 0.3650(3) 0.6376(3) 0.2679(3) 0.0349(9) Uani 1 1 d . . . . .
C5 C 0.2881(2) 0.6253(3) 0.3047(3) 0.0316(9) Uani 1 1 d . . . . .
C6 C 0.2894(3) 0.5673(3) 0.4129(3) 0.0319(9) Uani 1 1 d . . . . .
C7 C 0.2074(3) 0.5560(3) 0.4476(3) 0.0351(9) Uani 1 1 d . . . . .
H7 H 0.1457 0.5838 0.4016 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2362(2) 0.4985(3) 0.5570(3) 0.0344(9) Uani 1 1 d . . . . .
H8 H 0.1990 0.4796 0.6028 0.041 Uiso 1 1 calc R U . . .
C9 C 0.3364(2) 0.4709(3) 0.5917(3) 0.0301(9) Uani 1 1 d . . . . .
C10 C 0.3920(2) 0.4076(3) 0.7000(3) 0.0320(9) Uani 1 1 d . . . . .
C11 C 0.1957(2) 0.6794(3) 0.2190(3) 0.0348(9) Uani 1 1 d . . . . .
C12 C 0.1437(3) 0.6215(4) 0.1088(4) 0.0483(11) Uani 1 1 d . . . . .
C13 C 0.0591(3) 0.6719(5) 0.0274(4) 0.0628(12) Uani 1 1 d . . . . .
C14 C 0.0258(3) 0.7816(5) 0.0561(5) 0.0652(14) Uani 1 1 d . . . . .
C15 C 0.0742(3) 0.8411(4) 0.1650(5) 0.0626(13) Uani 1 1 d . . . . .
C16 C 0.1584(3) 0.7896(4) 0.2440(4) 0.0462(10) Uani 1 1 d . . . . .
C17 C 0.3461(3) 0.3699(3) 0.7887(3) 0.0368(10) Uani 1 1 d . . . . .
C18 C 0.2316(3) 0.2541(4) 0.8243(4) 0.0624(13) Uani 1 1 d . . . . .
H18 H 0.1812 0.1964 0.7970 0.075 Uiso 1 1 calc R U . . .
C19 C 0.2566(4) 0.3010(4) 0.9399(4) 0.0660(14) Uani 1 1 d . . . . .
H19 H 0.2246 0.2766 0.9909 0.079 Uiso 1 1 calc R U . . .
C20 C 0.3304(4) 0.3852(4) 0.9797(4) 0.0679(14) Uani 1 1 d . . . . .
H20 H 0.3499 0.4187 1.0594 0.081 Uiso 1 1 calc R U . . .
C21 C 0.3758(3) 0.4207(3) 0.9039(3) 0.0489(11) Uani 1 1 d . . . . .
H21 H 0.4261 0.4785 0.9306 0.059 Uiso 1 1 calc R U . . .
N1 N 0.4550(2) 0.5906(2) 0.3279(2) 0.0362(8) Uani 1 1 d . . . . .
H1 H 0.4731 0.5471 0.3955 0.043 Uiso 1 1 calc R U . . .
N2 N 0.36768(18) 0.5136(2) 0.5026(2) 0.0318(7) Uani 1 1 d . . . . .
N3 N 0.2742(2) 0.2846(3) 0.7453(3) 0.0552(9) Uani 1 1 d . . . . .
F1 F 0.17396(15) 0.5123(2) 0.07770(17) 0.0754(7) Uani 1 1 d . . . . .
F2 F 0.01123(16) 0.6128(3) -0.0803(2) 0.1057(10) Uani 1 1 d . . . . .
F3 F -0.05610(17) 0.8311(3) -0.0231(2) 0.1144(10) Uani 1 1 d . . . . .
F4 F 0.04209(17) 0.9507(2) 0.1932(2) 0.1046(9) Uani 1 1 d . . . . .
F5 F 0.20590(16) 0.8517(2) 0.3504(2) 0.0746(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.362(4) . ?
C1 C10 1.391(4) 3_666 ?
C1 C2 1.420(4) . ?
C2 C3 1.345(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.415(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.365(4) . ?
C4 C5 1.388(4) . ?
C5 C6 1.391(4) . ?
C5 C11 1.490(4) . ?
C6 N2 1.370(3) . ?
C6 C7 1.446(4) . ?
C7 C8 1.325(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.443(4) . ?
C8 H8 0.9300 . ?
C9 N2 1.365(3) . ?
C9 C10 1.392(4) . ?
C10 C1 1.391(4) 3_666 ?
C10 C17 1.496(4) . ?
C11 C16 1.365(4) . ?
C11 C12 1.368(4) . ?
C12 F1 1.333(4) . ?
C12 C13 1.377(5) . ?
C13 F2 1.340(4) . ?
C13 C14 1.347(5) . ?
C14 F3 1.339(4) . ?
C14 C15 1.353(5) . ?
C15 F4 1.336(4) . ?
C15 C16 1.370(5) . ?
C16 F5 1.342(4) . ?
C17 N3 1.351(4) . ?
C17 C21 1.352(4) . ?
C18 N3 1.343(4) . ?
C18 C19 1.346(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.360(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.356(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
N1 H1 0.8600 . ?

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
N1 C1 C10 126.0(3) . 3_666 ?
N1 C1 C2 106.5(3) . . ?
C10 C1 C2 127.4(3) 3_666 . ?
C3 C2 C1 108.3(3) . . ?
C3 C2 H2 125.8 . . ?
C1 C2 H2 125.8 . . ?
C2 C3 C4 108.3(3) . . ?
C2 C3 H3 125.8 . . ?
C4 C3 H3 125.8 . . ?
N1 C4 C5 126.7(3) . . ?
N1 C4 C3 106.7(3) . . ?
C5 C4 C3 126.6(3) . . ?
C4 C5 C6 126.2(3) . . ?
C4 C5 C11 116.2(3) . . ?
C6 C5 C11 117.6(3) . . ?
N2 C6 C5 125.7(3) . . ?
N2 C6 C7 109.8(3) . . ?
C5 C6 C7 124.5(3) . . ?
C8 C7 C6 107.4(3) . . ?
C8 C7 H7 126.3 . . ?
C6 C7 H7 126.3 . . ?
C7 C8 C9 106.9(3) . . ?
C7 C8 H8 126.5 . . ?
C9 C8 H8 126.5 . . ?
N2 C9 C10 125.4(3) . . ?
N2 C9 C8 110.4(3) . . ?
C10 C9 C8 124.1(3) . . ?
C1 C10 C9 125.6(3) 3_666 . ?
C1 C10 C17 116.3(3) 3_666 . ?
C9 C10 C17 118.1(3) . . ?
C16 C11 C12 116.0(3) . . ?
C16 C11 C5 122.6(3) . . ?
C12 C11 C5 121.4(3) . . ?
F1 C12 C11 120.0(4) . . ?
F1 C12 C13 117.9(4) . . ?
C11 C12 C13 122.1(4) . . ?
F2 C13 C14 120.4(5) . . ?
F2 C13 C12 120.0(5) . . ?
C14 C13 C12 119.6(4) . . ?
F3 C14 C13 119.7(5) . . ?
F3 C14 C15 119.9(5) . . ?
C13 C14 C15 120.3(4) . . ?
F4 C15 C14 120.6(4) . . ?
F4 C15 C16 120.4(5) . . ?
C14 C15 C16 119.0(4) . . ?
F5 C16 C11 119.1(4) . . ?
F5 C16 C15 117.9(4) . . ?
C11 C16 C15 123.0(4) . . ?
N3 C17 C21 123.4(3) . . ?
N3 C17 C10 115.8(3) . . ?
C21 C17 C10 120.8(4) . . ?
N3 C18 C19 124.7(4) . . ?
N3 C18 H18 117.7 . . ?
C19 C18 H18 117.7 . . ?
C18 C19 C20 117.6(4) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 H19 121.2 . . ?
C21 C20 C19 120.5(4) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C17 C21 C20 118.4(4) . . ?
C17 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
C1 N1 C4 110.2(3) . . ?
C1 N1 H1 124.9 . . ?
C4 N1 H1 124.9 . . ?
C9 N2 C6 105.5(3) . . ?
C18 N3 C17 115.3(3) . . ?

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
N1 C1 C2 C3 -1.0(4) . . . . ?
C10 C1 C2 C3 -179.3(3) 3_666 . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C2 C3 C4 N1 -0.5(4) . . . . ?
C2 C3 C4 C5 178.7(3) . . . . ?
N1 C4 C5 C6 3.0(5) . . . . ?
C3 C4 C5 C6 -176.0(3) . . . . ?
N1 C4 C5 C11 -176.8(3) . . . . ?
C3 C4 C5 C11 4.2(5) . . . . ?
C4 C5 C6 N2 0.8(5) . . . . ?
C11 C5 C6 N2 -179.4(3) . . . . ?
C4 C5 C6 C7 -179.7(3) . . . . ?
C11 C5 C6 C7 0.1(5) . . . . ?
N2 C6 C7 C8 1.0(4) . . . . ?
C5 C6 C7 C8 -178.5(3) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 N2 0.7(3) . . . . ?
C7 C8 C9 C10 -178.3(3) . . . . ?
N2 C9 C10 C1 -0.2(5) . . . 3_666 ?
C8 C9 C10 C1 178.7(3) . . . 3_666 ?
N2 C9 C10 C17 178.8(3) . . . . ?
C8 C9 C10 C17 -2.3(5) . . . . ?
C4 C5 C11 C16 -106.2(4) . . . . ?
C6 C5 C11 C16 74.0(4) . . . . ?
C4 C5 C11 C12 73.0(4) . . . . ?
C6 C5 C11 C12 -106.9(4) . . . . ?
C16 C11 C12 F1 -178.8(3) . . . . ?
C5 C11 C12 F1 1.9(5) . . . . ?
C16 C11 C12 C13 0.6(5) . . . . ?
C5 C11 C12 C13 -178.7(3) . . . . ?
F1 C12 C13 F2 -1.6(5) . . . . ?
C11 C12 C13 F2 179.0(3) . . . . ?
F1 C12 C13 C14 179.5(4) . . . . ?
C11 C12 C13 C14 0.1(6) . . . . ?
F2 C13 C14 F3 0.7(6) . . . . ?
C12 C13 C14 F3 179.6(3) . . . . ?
F2 C13 C14 C15 179.9(3) . . . . ?
C12 C13 C14 C15 -1.1(6) . . . . ?
F3 C14 C15 F4 -1.6(6) . . . . ?
C13 C14 C15 F4 179.2(4) . . . . ?
F3 C14 C15 C16 -179.3(3) . . . . ?
C13 C14 C15 C16 1.4(6) . . . . ?
C12 C11 C16 F5 -179.8(3) . . . . ?
C5 C11 C16 F5 -0.6(5) . . . . ?
C12 C11 C16 C15 -0.2(5) . . . . ?
C5 C11 C16 C15 179.0(3) . . . . ?
F4 C15 C16 F5 1.1(5) . . . . ?
C14 C15 C16 F5 178.8(3) . . . . ?
F4 C15 C16 C11 -178.5(3) . . . . ?
C14 C15 C16 C11 -0.8(6) . . . . ?
C1 C10 C17 N3 -117.4(3) 3_666 . . . ?
C9 C10 C17 N3 63.5(4) . . . . ?
C1 C10 C17 C21 63.2(4) 3_666 . . . ?
C9 C10 C17 C21 -115.8(4) . . . . ?
N3 C18 C19 C20 0.0(6) . . . . ?
C18 C19 C20 C21 0.6(6) . . . . ?
N3 C17 C21 C20 -0.7(5) . . . . ?
C10 C17 C21 C20 178.6(3) . . . . ?
C19 C20 C21 C17 -0.3(6) . . . . ?
C10 C1 N1 C4 179.0(3) 3_666 . . . ?
C2 C1 N1 C4 0.7(3) . . . . ?
C5 C4 N1 C1 -179.3(3) . . . . ?
C3 C4 N1 C1 -0.1(3) . . . . ?
C10 C9 N2 C6 179.0(3) . . . . ?
C8 C9 N2 C6 0.0(3) . . . . ?
C5 C6 N2 C9 178.9(3) . . . . ?
C7 C6 N2 C9 -0.6(3) . . . . ?
C19 C18 N3 C17 -0.8(6) . . . . ?
C21 C17 N3 C18 1.2(5) . . . . ?
C10 C17 N3 C18 -178.1(3) . . . . ?

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
C8 H8 F3 0.93 2.54 3.137(4) 122.5 2_545
N1 H1 N2 0.86 2.39 2.922(4) 120.6 .
N1 H1 N2 0.86 2.34 2.879(4) 121.5 3_666
C8 H8 F3 0.93 2.54 3.137(4) 122.5 2_545
N1 H1 N2 0.86 2.39 2.922(4) 120.6 .
N1 H1 N2 0.86 2.34 2.879(4) 121.5 3_666

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.042

# start Validation Reply Form 
_vrf_RINTA01_190                 
; 
PROBLEM: The value of Rint is greater than 0.18 
RESPONSE:Crystal was poorly diffracting at higher Bragg angles. 
Most of the reflections above 20 degrees foud to be 
with I < 2sigma(I). This has lead to large levell of measurement 
uncertainity for I at higher Bragg angles which leads to 
over all bad R(int). 
;
_vrf_THETM01_190                 
; 
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575 
RESPONSE:Crystal was poorly diffracting at higher Bragg angles. 
Recrystallisation and fresh data collection did not improve 
the situation. 
;
# end Validation Reply Form 

####################################################################### 
# 
# 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_PN187
_database_code_depnum_ccdc_archive 'CCDC 1443805'
_audit_update_record             
;
2016-05-02 deposited with the CCDC.
2016-06-22 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            'C42 H26 F10 N6 O4'
_chemical_formula_weight         868.69

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   31.4898(16)
_cell_length_b                   6.7009(3)
_cell_length_c                   22.5181(12)
_cell_angle_alpha                90
_cell_angle_beta                 122.093(2)
_cell_angle_gamma                90
_cell_volume                     4025.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6751
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      24.7

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_F_000             1768
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.957
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.93
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Sealed tube'
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22804
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -38
_diffrn_reflns_limit_h_max       38
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.135
_diffrn_reflns_theta_max         26.013
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3949
_reflns_number_gt                2500
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0783P)²+4.5588P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3949
_refine_ls_number_parameters     372
_refine_ls_number_restraints     244
_refine_ls_R_factor_all          0.0922
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1735
_refine_ls_wR_factor_gt          0.1392
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.006
_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
C1 C 0.31843(9) -0.1143(4) 1.07338(12) 0.0418(6) Uani 1 1 d . . . . .
C2 C 0.36309(10) -0.2052(4) 1.08335(14) 0.0532(7) Uani 1 1 d . . . . .
H2 H 0.3790 -0.3182 1.1100 0.064 Uiso 1 1 calc R U . . .
C3 C 0.37753(10) -0.0971(4) 1.04729(15) 0.0572(8) Uani 1 1 d . . . . .
H3 H 0.4053 -0.1219 1.0440 0.069 Uiso 1 1 calc R U . . .
C4 C 0.34264(9) 0.0636(4) 1.01454(13) 0.0433(6) Uani 1 1 d . . . . .
C5 C 0.34608(9) 0.2134(4) 0.97427(13) 0.0439(6) Uani 1 1 d . . . . .
C6 C 0.31404(9) 0.3744(4) 0.94199(13) 0.0449(6) Uani 1 1 d . . . . .
C7 C 0.31816(10) 0.5218(4) 0.89990(15) 0.0569(7) Uani 1 1 d . . . . .
H7 H 0.3431 0.5283 0.8897 0.068 Uiso 1 1 calc R U . . .
C8 C 0.27984(10) 0.6499(4) 0.87744(15) 0.0564(7) Uani 1 1 d . . . . .
H8 H 0.2734 0.7602 0.8487 0.068 Uiso 1 1 calc R U . . .
C9 C 0.25075(9) 0.5858(4) 0.90577(13) 0.0429(6) Uani 1 1 d . . . . .
C10 C 0.20749(9) 0.6764(4) 0.89529(12) 0.0406(6) Uani 1 1 d D . . . .
C11 C 0.39106(9) 0.2062(4) 0.96797(14) 0.0454(6) Uani 1 1 d . . . . .
C12 C 0.43603(11) 0.2873(4) 1.01972(16) 0.0551(7) Uani 1 1 d . . . . .
C13 C 0.47796(11) 0.2833(5) 1.01570(19) 0.0656(9) Uani 1 1 d . . . . .
C14 C 0.47466(12) 0.2020(4) 0.9575(2) 0.0650(9) Uani 1 1 d . . . . .
C15 C 0.43107(13) 0.1202(4) 0.90571(18) 0.0631(8) Uani 1 1 d . . . . .
C16 C 0.38986(10) 0.1220(4) 0.91141(15) 0.0523(7) Uani 1 1 d . . . . .
C17 C 0.1852(3) 0.8423(9) 0.8437(3) 0.0421(14) Uani 0.828(7) 1 d D U P A 6
C18 C 0.16844(19) 0.8044(8) 0.7746(2) 0.0597(12) Uani 0.828(7) 1 d D U P A 6
H18 H 0.1727 0.6762 0.7628 0.072 Uiso 0.828(7) 1 calc R U P A 6
C19 C 0.1406(3) 1.1211(11) 0.7414(4) 0.075(2) Uani 0.828(7) 1 d D U P A 6
H19 H 0.1248 1.2170 0.7064 0.090 Uiso 0.828(7) 1 calc R U P A 6
C20 C 0.15675(18) 1.1746(5) 0.8085(2) 0.0708(13) Uani 0.828(7) 1 d D U P A 6
H20 H 0.1525 1.3047 0.8188 0.085 Uiso 0.828(7) 1 calc R U P A 6
C21 C 0.17931(16) 1.0339(5) 0.86069(19) 0.0569(11) Uani 0.828(7) 1 d D U P A 6
H21 H 0.1904 1.0672 0.9068 0.068 Uiso 0.828(7) 1 calc R U P A 6
N3 N 0.1464(2) 0.9391(9) 0.7233(3) 0.0746(17) Uani 0.828(7) 1 d D U P A 6
C17' C 0.1876(19) 0.836(4) 0.8411(16) 0.052(7) Uani 0.172(7) 1 d D U P A 7
C18' C 0.1469(9) 0.805(4) 0.7761(12) 0.068(6) Uani 0.172(7) 1 d D U P A 7
H18' H 0.1320 0.6802 0.7690 0.081 Uiso 0.172(7) 1 calc R U P A 7
C19' C 0.1495(15) 1.098(6) 0.737(2) 0.077(7) Uani 0.172(7) 1 d D U P A 7
H19' H 0.1384 1.1871 0.6997 0.092 Uiso 0.172(7) 1 calc R U P A 7
C20' C 0.1884(10) 1.160(3) 0.7992(10) 0.084(6) Uani 0.172(7) 1 d D U P A 7
H20' H 0.2007 1.2895 0.8066 0.101 Uiso 0.172(7) 1 calc R U P A 7
C21' C 0.2082(9) 1.020(2) 0.8507(10) 0.072(5) Uani 0.172(7) 1 d D U P A 7
H21' H 0.2368 1.0508 0.8937 0.086 Uiso 0.172(7) 1 calc R U P A 7
N3' N 0.1251(11) 0.926(5) 0.7215(16) 0.096(13) Uani 0.172(7) 1 d D . P A 7
N1 N 0.30646(8) 0.0480(3) 1.03032(11) 0.0424(5) Uani 1 1 d D . . . .
N2 N 0.27282(7) 0.4188(3) 0.94510(11) 0.0421(5) Uani 1 1 d D . . . .
F1 F 0.43896(7) 0.3730(3) 1.07529(10) 0.0831(6) Uani 1 1 d . . . . .
F2 F 0.52116(7) 0.3590(3) 1.06719(13) 0.0973(7) Uani 1 1 d . . . . .
F3 F 0.51536(7) 0.2029(3) 0.95269(14) 0.1030(8) Uani 1 1 d . . . . .
F4 F 0.42885(9) 0.0384(3) 0.85016(12) 0.0961(7) Uani 1 1 d . . . . .
F5 F 0.34752(7) 0.0389(3) 0.86012(9) 0.0748(6) Uani 1 1 d . . . . .
H2A H 0.2606(15) 0.352(6) 0.965(2) 0.026(11) Uiso 0.5 1 d D . P . .
H1A H 0.2809(15) 0.123(8) 1.017(3) 0.070(19) Uiso 0.5 1 d D . P . .
O1 O 0.5094(10) 0.653(6) 1.2367(14) 0.250(11) Uani 0.442(18) 1 d . U P B 1
O2 O 0.5000 0.250(6) 1.2500 0.265(10) Uani 0.70(3) 2 d S TU P C 2
O3 O 0.5154(7) 0.444(6) 1.2500(10) 0.200(8) Uani 0.370(16) 1 d . U P D 3
O4 O 0.5144(8) 0.057(6) 1.2431(11) 0.250(9) Uani 0.472(17) 1 d . U P E 4
O5 O 0.5104(9) -0.148(6) 1.2422(12) 0.196(10) Uani 0.366(18) 1 d . U P F 5


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.370(3) . ?
C1 C10 1.396(3) 7_557 ?
C1 C2 1.437(3) . ?
C2 C3 1.335(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.432(4) . ?
C3 H3 0.9300 . ?
C4 N1 1.366(3) . ?
C4 C5 1.395(3) . ?
C5 C6 1.390(3) . ?
C5 C11 1.498(3) . ?
C6 N2 1.369(3) . ?
C6 C7 1.422(4) . ?
C7 C8 1.342(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.432(3) . ?
C8 H8 0.9300 . ?
C9 N2 1.366(3) . ?
C9 C10 1.392(3) . ?
C10 C1 1.396(3) 7_557 ?
C10 C17 1.488(5) . ?
C10 C17' 1.488(17) . ?
C11 C16 1.375(4) . ?
C11 C12 1.380(4) . ?
C12 F1 1.335(3) . ?
C12 C13 1.371(4) . ?
C13 F2 1.333(4) . ?
C13 C14 1.372(5) . ?
C14 F3 1.342(3) . ?
C14 C15 1.357(5) . ?
C15 F4 1.333(3) . ?
C15 C16 1.370(4) . ?
C16 F5 1.336(3) . ?
C17 C18 1.375(9) . ?
C17 C21 1.380(9) . ?
C18 N3 1.334(5) . ?
C18 H18 0.9300 . ?
C19 N3 1.329(8) . ?
C19 C20 1.361(8) . ?
C19 H19 0.9300 . ?
C20 C21 1.374(5) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C17' C18' 1.354(18) . ?
C17' C21' 1.355(18) . ?
C18' N3' 1.320(16) . ?
C18' H18' 0.9300 . ?
C19' N3' 1.323(17) . ?
C19' C20' 1.35(2) . ?
C19' H19' 0.9300 . ?
C20' C21' 1.358(17) . ?
C20' H20' 0.9300 . ?
C21' H21' 0.9300 . ?
N1 H1A 0.86(2) . ?
N2 H2A 0.860(19) . ?
O1 O1 1.04(4) 2_657 ?
O3 O3 0.97(3) 2_657 ?
O4 O4 1.10(3) 2_657 ?
O5 O5 0.89(3) 2_657 ?

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
N1 C1 C10 125.4(2) . 7_557 ?
N1 C1 C2 109.0(2) . . ?
C10 C1 C2 125.5(2) 7_557 . ?
C3 C2 C1 107.2(2) . . ?
C3 C2 H2 126.4 . . ?
C1 C2 H2 126.4 . . ?
C2 C3 C4 107.8(2) . . ?
C2 C3 H3 126.1 . . ?
C4 C3 H3 126.1 . . ?
N1 C4 C5 126.0(2) . . ?
N1 C4 C3 109.1(2) . . ?
C5 C4 C3 124.9(2) . . ?
C6 C5 C4 127.8(2) . . ?
C6 C5 C11 115.8(2) . . ?
C4 C5 C11 116.3(2) . . ?
N2 C6 C5 125.9(2) . . ?
N2 C6 C7 107.9(2) . . ?
C5 C6 C7 126.2(2) . . ?
C8 C7 C6 108.3(2) . . ?
C8 C7 H7 125.9 . . ?
C6 C7 H7 125.9 . . ?
C7 C8 C9 107.5(2) . . ?
C7 C8 H8 126.3 . . ?
C9 C8 H8 126.3 . . ?
N2 C9 C10 125.6(2) . . ?
N2 C9 C8 108.0(2) . . ?
C10 C9 C8 126.4(2) . . ?
C9 C10 C1 124.5(2) . 7_557 ?
C9 C10 C17 118.1(6) . . ?
C1 C10 C17 117.3(5) 7_557 . ?
C9 C10 C17' 114(3) . . ?
C1 C10 C17' 122(3) 7_557 . ?
C16 C11 C12 117.0(2) . . ?
C16 C11 C5 122.6(2) . . ?
C12 C11 C5 120.3(2) . . ?
F1 C12 C13 118.7(3) . . ?
F1 C12 C11 119.3(2) . . ?
C13 C12 C11 121.9(3) . . ?
F2 C13 C12 120.6(3) . . ?
F2 C13 C14 120.4(3) . . ?
C12 C13 C14 119.0(3) . . ?
F3 C14 C15 120.4(3) . . ?
F3 C14 C13 119.0(3) . . ?
C15 C14 C13 120.6(3) . . ?
F4 C15 C14 119.8(3) . . ?
F4 C15 C16 120.7(3) . . ?
C14 C15 C16 119.5(3) . . ?
F5 C16 C15 118.4(3) . . ?
F5 C16 C11 119.7(2) . . ?
C15 C16 C11 121.9(3) . . ?
C18 C17 C21 117.3(4) . . ?
C18 C17 C10 119.0(7) . . ?
C21 C17 C10 123.7(6) . . ?
N3 C18 C17 124.4(6) . . ?
N3 C18 H18 117.8 . . ?
C17 C18 H18 117.8 . . ?
N3 C19 C20 123.5(7) . . ?
N3 C19 H19 118.3 . . ?
C20 C19 H19 118.3 . . ?
C19 C20 C21 119.1(5) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 H20 120.4 . . ?
C20 C21 C17 119.0(4) . . ?
C20 C21 H21 120.5 . . ?
C17 C21 H21 120.5 . . ?
C19 N3 C18 116.6(7) . . ?
C18' C17' C21' 114.2(18) . . ?
C18' C17' C10 121.3(17) . . ?
C21' C17' C10 124.4(16) . . ?
N3' C18' C17' 130(2) . . ?
N3' C18' H18' 115.2 . . ?
C17' C18' H18' 115.2 . . ?
N3' C19' C20' 128(4) . . ?
N3' C19' H19' 115.9 . . ?
C20' C19' H19' 115.9 . . ?
C19' C20' C21' 115(3) . . ?
C19' C20' H20' 122.3 . . ?
C21' C20' H20' 122.3 . . ?
C17' C21' C20' 121.8(18) . . ?
C17' C21' H21' 119.1 . . ?
C20' C21' H21' 119.1 . . ?
C18' N3' C19' 111(3) . . ?
C4 N1 C1 106.91(19) . . ?
C4 N1 H1A 128(4) . . ?
C1 N1 H1A 125(4) . . ?
C9 N2 C6 108.3(2) . . ?
C9 N2 H2A 123(3) . . ?
C6 N2 H2A 128(3) . . ?

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
N1 C1 C2 C3 0.6(3) . . . . ?
C10 C1 C2 C3 -177.1(3) 7_557 . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 N1 -1.2(3) . . . . ?
C2 C3 C4 C5 177.6(3) . . . . ?
N1 C4 C5 C6 -0.4(4) . . . . ?
C3 C4 C5 C6 -179.0(3) . . . . ?
N1 C4 C5 C11 176.2(2) . . . . ?
C3 C4 C5 C11 -2.4(4) . . . . ?
C4 C5 C6 N2 1.5(5) . . . . ?
C11 C5 C6 N2 -175.1(2) . . . . ?
C4 C5 C6 C7 -178.4(3) . . . . ?
C11 C5 C6 C7 5.0(4) . . . . ?
N2 C6 C7 C8 -0.9(3) . . . . ?
C5 C6 C7 C8 179.0(3) . . . . ?
C6 C7 C8 C9 0.5(3) . . . . ?
C7 C8 C9 N2 0.1(3) . . . . ?
C7 C8 C9 C10 -179.8(3) . . . . ?
N2 C9 C10 C1 3.3(4) . . . 7_557 ?
C8 C9 C10 C1 -176.9(3) . . . 7_557 ?
N2 C9 C10 C17 -172.4(3) . . . . ?
C8 C9 C10 C17 7.4(5) . . . . ?
N2 C9 C10 C17' -170.7(12) . . . . ?
C8 C9 C10 C17' 9.1(12) . . . . ?
C6 C5 C11 C16 -85.8(3) . . . . ?
C4 C5 C11 C16 97.2(3) . . . . ?
C6 C5 C11 C12 93.7(3) . . . . ?
C4 C5 C11 C12 -83.3(3) . . . . ?
C16 C11 C12 F1 179.2(2) . . . . ?
C5 C11 C12 F1 -0.3(4) . . . . ?
C16 C11 C12 C13 -0.5(4) . . . . ?
C5 C11 C12 C13 179.9(2) . . . . ?
F1 C12 C13 F2 1.7(4) . . . . ?
C11 C12 C13 F2 -178.6(3) . . . . ?
F1 C12 C13 C14 -177.6(3) . . . . ?
C11 C12 C13 C14 2.1(4) . . . . ?
F2 C13 C14 F3 -1.1(4) . . . . ?
C12 C13 C14 F3 178.2(2) . . . . ?
F2 C13 C14 C15 178.3(3) . . . . ?
C12 C13 C14 C15 -2.3(5) . . . . ?
F3 C14 C15 F4 0.7(4) . . . . ?
C13 C14 C15 F4 -178.7(3) . . . . ?
F3 C14 C15 C16 -179.6(2) . . . . ?
C13 C14 C15 C16 1.0(5) . . . . ?
F4 C15 C16 F5 0.3(4) . . . . ?
C14 C15 C16 F5 -179.4(3) . . . . ?
F4 C15 C16 C11 -179.7(3) . . . . ?
C14 C15 C16 C11 0.7(4) . . . . ?
C12 C11 C16 F5 179.1(2) . . . . ?
C5 C11 C16 F5 -1.3(4) . . . . ?
C12 C11 C16 C15 -0.9(4) . . . . ?
C5 C11 C16 C15 178.6(2) . . . . ?
C9 C10 C17 C18 61.9(8) . . . . ?
C1 C10 C17 C18 -114.1(9) 7_557 . . . ?
C9 C10 C17 C21 -119.5(9) . . . . ?
C1 C10 C17 C21 64.4(8) 7_557 . . . ?
C21 C17 C18 N3 -0.9(12) . . . . ?
C10 C17 C18 N3 177.7(6) . . . . ?
N3 C19 C20 C21 -1.4(10) . . . . ?
C19 C20 C21 C17 0.3(9) . . . . ?
C18 C17 C21 C20 0.7(11) . . . . ?
C10 C17 C21 C20 -177.9(6) . . . . ?
C20 C19 N3 C18 1.2(11) . . . . ?
C17 C18 N3 C19 0.0(10) . . . . ?
C9 C10 C17' C18' 104(6) . . . . ?
C1 C10 C17' C18' -70(7) 7_557 . . . ?
C9 C10 C17' C21' -75(7) . . . . ?
C1 C10 C17' C21' 111(6) 7_557 . . . ?
C21' C17' C18' N3' 1(9) . . . . ?
C10 C17' C18' N3' -178(4) . . . . ?
N3' C19' C20' C21' 8(7) . . . . ?
C18' C17' C21' C20' 2(8) . . . . ?
C10 C17' C21' C20' -180(4) . . . . ?
C19' C20' C21' C17' -5(6) . . . . ?
C17' C18' N3' C19' 1(7) . . . . ?
C20' C19' N3' C18' -6(7) . . . . ?
C5 C4 N1 C1 -177.2(3) . . . . ?
C3 C4 N1 C1 1.6(3) . . . . ?
C10 C1 N1 C4 176.4(2) 7_557 . . . ?
C2 C1 N1 C4 -1.3(3) . . . . ?
C10 C9 N2 C6 179.2(2) . . . . ?
C8 C9 N2 C6 -0.6(3) . . . . ?
C5 C6 N2 C9 -179.0(3) . . . . ?
C7 C6 N2 C9 0.9(3) . . . . ?

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
C3 H3 F3 0.93 2.52 3.446(3) 174.3 5_657
C19 H19 F4 0.93 2.61 3.474(8) 154.1 4_566
C18' H18' F4 0.93 2.51 3.12(2) 123.7 4_556
N2 H2A N1 0.860(19) 2.48(4) 2.969(3) 117(3) .
N2 H2A N1 0.860(19) 2.27(4) 2.838(3) 124(3) 7_557
N1 H1A N2 0.86(2) 2.48(6) 2.969(3) 117(5) .
N1 H1A N2 0.86(2) 2.29(5) 2.838(3) 122(5) 7_557
C3 H3 F3 0.93 2.52 3.446(3) 174.3 5_657
C19 H19 F4 0.93 2.61 3.474(8) 154.1 4_566
C18' H18' F4 0.93 2.51 3.12(2) 123.7 4_556
N2 H2A N1 0.860(19) 2.48(4) 2.969(3) 117(3) .
N2 H2A N1 0.860(19) 2.27(4) 2.838(3) 124(3) 7_557
N1 H1A N2 0.86(2) 2.48(6) 2.969(3) 117(5) .
N1 H1A N2 0.86(2) 2.29(5) 2.838(3) 122(5) 7_557

_refine_diff_density_max         0.283
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.056

